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CAS No. : | 1224724-39-3 | MDL No. : | MFCD20487964 |
Formula : | C10H8BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JTBLJEGYYYHKGQ-UHFFFAOYSA-N |
M.W : | 254.08 | Pubchem ID : | 58315919 |
Synonyms : |
|
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 |
---|---|---|
33% | In tetrahydrofuran; at -60 - -30℃; for 2h;Inert atmosphere; | To a solution of <strong>[158580-57-5]methyl 4-bromo-2-nitrobenzoate</strong> (10 g, 38.4 mmol, 1 eq) in 60 mL of dry THF was added vinylmagnesium bromide (1.0 M in THF, 136 mL, 136 mmol, 3.5 eq) dropwise at -60 C under nitrogen. The reaction mixture was stirred at -30 C ~ -40 C for 2h. Then the mixture was treated with saturated aq. NH4Cl (50 mL), the resulting mixture was extracted with EtOAc (50 mL × 3), the combined organic phase was washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4, and concentrated. The residue was purified by column chromatography to afford methyl 4-bromoindole-7-carboxylate (3.2 g, 33%). 1HNMR (300 MHz, CDCl3): G 9.98 (br, 1H), 7.76- 7.73 (m, 1 H), 7.39- 7.33 (m, 2 H), 6.67 (s, 1 H), 4.00 (s, 3 H). LCMS: (M-H)-: 251.8 |
31% | General Procedure I-ETTo a solution of <strong>[158580-57-5]methyl 4-bromo-2-nitrobenzoate</strong> (I-XVIIa, 5 g, 19 mmol) in 30 mL of dry THF was added vinylmagnesium bromide (1.0 M in THF, 48 mL, 48 mmol) dropwise at -60 C. under Nitrogen. The reaction mixture was stirred at room temperature overnight. Then the mixture was treated with saturated aq. NH4Cl, the resulting mixture was extracted with EtOAc (50 mL×2), the organic phase was washed with water (100 mL), brine (100 mL), dried over anhydrous Na2SO4, and concentrated. The residue was purified by column chromatography to afford compound I-XVIIb (1.5 g, yield 31%). 1H NMR (400 MHz, CDCl3) delta 9.90 (s, 1H), 7.66 (d, J=8.0 Hz, 1H), 7.52-7.30 (m, 2H), 6.58 (t, J=2.8 Hz, 1H), 3.91 (s, 3H). | |
30% | In tetrahydrofuran; at -60 - -40℃; for 2h; | A solution of compound 267b (2.5 g, 9.614 mmol) in tetrahydrofuran (15 mL) was cooled to -60 C, and vinyl magnesium bromide (1.0 M in tetrahydrofuran, 34 mL, 34 mmol, 3.5 equivalents) was added dropwise to the solution under a nitrogen atmosphere. ). The reaction solution was stirred at -40 C for 2 hours. The reaction solution was then treated with a saturated aqueous ammonium chloride solution (30 mL), and the resulting mixture was extracted with ethyl acetate (80 mL × 3).The combined organic phases were washed with water (60 mL), brine (60 mL),It was dried over anhydrous sodium sulfate and then purified by silica gel chromatography (petroleum ether: ethyl acetate = 97: 3) to obtain a white solid compound 267c, which is methyl 4-bromo-1H-indole-7-carboxylic acid (850 mg, 30% yield). |
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