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[ CAS No. 4133-72-6 ] {[proInfo.proName]}

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Chemical Structure| 4133-72-6
Chemical Structure| 4133-72-6
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Product Details of [ 4133-72-6 ]

CAS No. :4133-72-6 MDL No. :MFCD27939807
Formula : C8H6BrFO3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :MCMGUPTVQMMNDL-UHFFFAOYSA-N
M.W : 249.03 Pubchem ID :67234801
Synonyms :

Safety of [ 4133-72-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4133-72-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4133-72-6 ]

[ 4133-72-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 4133-72-6 ]
  • [ 100-39-0 ]
  • [ 1159940-06-3 ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate; In acetone; for 12.0h;Reflux; A suspension of 12.7 g (51 mmol) methyl-5-bromo-4-fluoro-2-hydroxybenzoate, 6.7 ml (56.1 mmol) benzyl bromide and 14.01 g (102 mmol) potassium carbonate in 100 ml acetone is heated for 12 hours under reflux. After cooling, the potassium carbonate is filtered and washed with acetone, the solvent is removed under vacuum, and the raw product is purified by way of column chromatography on silica gel using diethyl ether/petroleum ether 1:3.Form: colorless solid matterYield: 13.14 g (38.76 mmol; 76%)Rf: 0.58 (diethyl ether/petrol ether=1:3).
  • 2
  • [ 1644-71-9 ]
  • [ 18107-18-1 ]
  • [ 4133-72-6 ]
YieldReaction ConditionsOperation in experiment
99% With methanol; In dichloromethane; at 20℃; for 0.5h; 1.23 g (5.2 mmol) 5-bromine-4-fluoro-2-hydroxybenzoic acid is dissolved in 10 ml anhydrous dichloromethane and 2 ml absolute methanol, mixed with 3.4 ml (6.76 mmol) trimethylsilyl diazomethane, and stirred for 30 minutes at room temperature. The volatile constituents are removed under vacuum and the product is obtained in pure form.Form: colorless solid matterYield: 1.27 g (5.1 mmol; 99%)Rf: 0.85 (diethyl ether/petroleum ether=1:2).
  • 3
  • [ 67-56-1 ]
  • [ 1644-71-9 ]
  • [ 4133-72-6 ]
YieldReaction ConditionsOperation in experiment
91.1% With sulfuric acid; at 85℃; for 32.0h; Intermediate 5 (29.0g, 123.4mmol) was dissolved in methanol (300mL), concentrated sulfuric acid (10.0mL) was added, and reacted at 85C for 32 hours. After the reaction was completed, the reaction solution was concentrated to dryness and the dichloromethane was renewed. Dissolved, the organic phase was washed with water, saturated sodium bicarbonate aqueous solution and brine in turn, dried over anhydrous sodium sulfate, filtered and concentrated to obtain Intermediate 6, 28.0 g of white solid, yield: 91.1%.
88% With sulfuric acid; at 80℃; for 17.0h; To a stirred mixture of 5-bromo-4-fluoro-2-hydroxybenzoic acid (75 g, 0.32 mol) in MeOH (800 mL) was added H2S04 (80 mL). The reaction mixture was stirred at 80 C for 17 h. After this time the volatiles were removed under reduced pressure and the resulting residue was dissolved in H20 (200 mL). The pH was adjusted to 10 - 11 by addition of aqueous NaOH and the aqueous layer was extrated with DCM (3 x 200 mL). The combined organic extracts were dried over Na2S04, filtered and concentrated to give the title compound (70 g, 88%) as a white solid. 1H NMR (400 MHz, DMSO-i) δ ppm 10.84 (br s, 1H), 8.01 (d, 7=8.0 Hz, 1H), 7.06 (d, 7=10.5 Hz, 1H), 3.88 (s, 3H).
75% With sulfuric acid; at 80℃; for 16.0h; [00327] To a solution of Example 28b (7 g, 29.3 mmol) in MeOH (50 mL) was added con.H2S04 (4 mL) dropwise at r.t., which was then stirred at 80C for 16 h. The mixture was concentrated to remove MeOH, diluted with water, extracted with EtOAc, dried, concentrated and purified by silica gel chromatography (Petroleum Ether/EtOAc = 100/5) to give Example 28c (5.5 g, yield 75%). LCMS [M+l]+=250.9.
1.4 g With sulfuric acid; at 70℃; for 24.0h; Taking compound 2 c (1.86 g, 7.9 mmol) dissolved in methanol (20 ml) in, slowly adding concentrated sulfuric acid (3 ml), 70 C heating 24 h. TLC monitoring display after the reaction. The reaction liquid concentrated, residue of ethyl acetate (50 ml) dissolved, saturated sodium bicarbonate solution to adjust pH to and 7 - 8, organic phase to saturated salt water (50 ml x 2) washing, drying with anhydrous sodium sulfate. Evaporate the solvent under reduced pressure. The residue by silica gel column chromatography (petroleum ether: ethyl acetate=200:1) purification to obtain compound 3 c (white solid, 1.4 g, yield 71%).

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Technical Information

? Acidity of Phenols ? Acyl Group Substitution ? Alkyl Halide Occurrence ? Appel Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Complex Metal Hydride Reductions ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Electrophilic Substitution of the Phenol Aromatic Ring ? Ester Cleavage ? Etherification Reaction of Phenolic Hydroxyl Group ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Halogenation of Phenols ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alcohols ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Reimer-Tiemann Reaction ? Ritter Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Swern Oxidation ? Vilsmeier-Haack Reaction
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