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CAS No. : | 673-22-3 | MDL No. : | MFCD00003327 |
Formula : | C8H8O3 | Boiling Point : | - |
Linear Structure Formula : | (OH)C6H3(CHO)OCH3 | InChI Key : | WZUODJNEIXSNEU-UHFFFAOYSA-N |
M.W : | 152.15 | Pubchem ID : | 69600 |
Synonyms : |
4-Methoxysalicylaldehyde;NSC 155334
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With bromine; acetic acid; at 0 - 20℃; for 2h; | In a 250 mL flask, 2-hydroxy-4-methoxybenzaldehyde (5 g, 32.9 mmol) was dissolved in acetic acid (65.7 mL), and cooled to 0 C, then Br2 (1 .862 ml, 36.1 mmol) in 10 mL acetic acid was added slowly. Upon complete addition, the reaction mixture was allowed to warm to room temperature, and stirred for 2 h. 100 mL of water was added to reaction flask, and the resulting white precipitate was filtered and washed with water. Drying under vacuum afforded the title compound (6.8 g, 29.4 mmol, 90 % yield). MS (M+1 ) = 233.3. 1H NMR (400 MHz, CHLOROFORM-d) delta 1 1.45 (s, 1 H), 9.70 (s, 1 H), 7.69 (s, 1 H), 6.49 (s, 1 H), 3.96 (s, 3H). |
87% | With bromine; acetic acid; at 0 - 20℃; for 1h; | To a solution of a commercially available 2-hydroxy-4-methoxybenzaldehyde (1.18 g, 7.76 mmol) in glacial acetic acid (15 mL) was added a solution of Br2 (0.44 mL, 8.62 mmol) in glacial acetic acid (5 mL) at 0 C and the reaction mixture was warmed up and stirred at room temperature for 1 h. Water (30 mL) was added and the precipitate was collected by filtration. Water (30 mL) and CH2Cl2 (30 mL) were added to the white solid and the two phases were separated. The aqueous layer was extracted with CH2Cl2 (3 x 25 mL) and the combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product 5-bromo-2-hydroxy-4-methoxybenzaldehyde which was further recrystallized from CH2Cl2 to furnish the desired product as a white solid (1.56 g, 6.75 mmol, 87 %). |
80% | With bromine; In dichloromethane; at 0 - 20℃; for 3h; | 2-HYDROXY-4-METHOXYBENZALDEHYDE (6.0 g, 39 mmol) was dissolved in dichloromethane (50 ML) and cooled to 0 C using an ice-water bath. Bromine (6.8 g, 43 mmol) in dichloromethane (2 mL) was added dropwise to the cooled solution and stirred for 2 h at 0 C. The mixture was warmed to room temperature and stirred for an additional 1 h and the resulting yellow precipitate was collected. Recrystallization (ethyl acetate/hexanes) yielded 7.1 g (80%) of 5-bromo-2-hydroxy-4- methoxybenzaldehyde as white needles, m. p. 63-64'C.'H-NMR (300 MHz, CDC13) 6 11.43 (s, 1 H), 9.69 (s, 1 H), 7.68 (s, 1 H), 6.48 (s, 1 H), 3.95 (s, 3 H). Anal. Calcd. for C8H7BRO3 : C, 41.59 ; H, 3.05. Found: C, 41.86 ; H, 3.05. |
76% | With tetra-n-butylammonium tribromide; sodium hydrogencarbonate; sodium chloride; In dichloromethane; water; | a. 3-Bromo-6-hydroxy-4-methoxy-benzaldehyde. A mixture of 2-hydroxy-4-methoxy-benzaldehyde (3.04 g, 20 mmol) and tetrabutylammonium tribromide (6.40 g, 20 mmol) in anhydrous dichloromethane (200 mL) was stirred at room temperature for 24 hours. The solution was washed successively with a saturated aqueous solution of NaHCO3 (150 mL), water (150 mL), a saturated aqueous solution of NaCl (150 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave a solid which was purified by column chromatography, using a Biotage 40M cartridge, eluding with 5% ethyl acetate/95% hexane to give 3-bromo-6-hydroxy-4-methoxy-benzaldehyde as a white solid (3.50 g, 76%). 1H NMR (500 MHz; CDCl3): delta3.94 (s, 3 H), 6.47 (s, 1 H), 7.67 (s, 1 H), 9.68 (s, 1 H), 11.43 (s, 1 H). |
76% | With tetra-n-butylammonium tribromide; sodium hydrogencarbonate; sodium chloride; In dichloromethane; water; | a. 3-Bromo-6-hydroxy-4-methoxy-benzaldehyde A mixture of 2-hydroxy-4-methoxy-benzaldehyde (3.04 g, 20 mmol) and tetrabutylammonium tribromide (6.40 g, 20 mmol) in anhydrous dichloromethane (200 mL) was stirred at room temperature for 24 hours. The solution was washed successively with a saturated aqueous solution of NaHCO3 (150 mL), water (150 mL), a saturated aqueous solution of NaCl (150 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave a solid which was purified by column chromatography, using a Biotage 40M cartridge, eluding with 5% ethyl acetate/95% hexane to give 3-bromo-6-hydroxy-4-methoxy-benzaldehyde as a white solid (3.50 g, 76%). 1H NMR (500 MHz; CDCl3): delta3.94 (s, 3H), 6.47 (s, 1H), 7.67 (s, 1H), 9.68 (s, 1H), 11.43 (s, 1H). |
With bromine; In dichloromethane; ethyl acetate; | Example 62 3-[5-(Benzo[b]thien-2-yl)-2-carboxymethoxy-4-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one, Sodium Salt Ex-62A: A solution of 2-hydroxy-4-methoxybenzaldehyde (3.03 g, 20 mmol) in 25 mL of dichloromethane was cooled to 0 C. and treated dropwise with a solution of bromine (3.41 g, 21 mmol) in 10 mL of dichloromethane. The reaction mixture was stirred at 0 C. for 1.5 hours. The solvent was removed by rotary evaporation to give a residue. The residue was taken up in EtOAc and washed with 3 portions of water. The organic layer was dried over MgSO4. The drying agent was removed by filtration, and solvent was removed by rotary evaporation to give 3.9 g of the desired 5-bromo-2-hydroxy-4-methoxybenzaldehyde as a solid, m.p. 111-115 C. | |
With bromine; | 2-Hydroxy-4-methoxybenzaldehyde (20 g, 131.4 mmol) was brominated to give 5-bromo-2-hydroxy-4-methoxybenzaldehyde as a light yellow solid, followed by coupling with 4-methoxyphenylboronic acid (750 mg, 4.94 mmol) using method A to give 800 mg (75%) of 4-hydroxy-6,4'-dimethoxybiphenyl-3-carbaldehyde as a light yellow solid. |