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CAS No. : | 16420-39-6 | MDL No. : | MFCD09841652 |
Formula : | C6H6BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XFBMRYPQVXPYQB-UHFFFAOYSA-N |
M.W : | 204.02 | Pubchem ID : | 23271158 |
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 |
---|---|---|
62% | With pyridine; N-Bromosuccinimide In tetrahydrofuran at -78℃; for 1 h; | Reference Example 22 methyl 5-bromo-1H-pyrrole-3-carboxylate; A solution (30 mL) of methyl 1H-pyrrole-3-carboxylate (3.06 g) in tetrahydrofuran was cooled to -78° C., N-bromosuccinimide (4.38 g) and then pyridine (3 drops) were added, and the mixture was stirred at the same temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=5:1) to give the title compound as a pale-yellow solid (yield 3.08 g, 62percent). 1H-NMR (CDCl3) δ: 3.81 (3H, s), 6.58 (1H, m), 7.36 (1H, m), 8.60 (1H, brs). |
49% | With pyridine; N-Bromosuccinimide In tetrahydrofuran at -78 - -20℃; for 72 h; | A solution of methyl 1H-pyrrole-3-carboxylate (4.48 g, 35.8 mmol) in THF (70 mL) was cooled to -78 °C, N-bromosuccinimide (6.30 g, 35.4 mmol) was added, pyridine (five drops) was added, and the mixture was left standing in a freezer (-20 °C) for 3 days. The reaction mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-EtOAc = 9/1-1/1) to give 12b (3.59 g, 49percent) as a pale-yellow solid: 1H NMR (CDCl3) δ 3.81 (3H, s), 6.58 (1H, m), 7.36 (1H, m), 8.60 (1H, br s). |
49% | With pyridine; N-Bromosuccinimide In tetrahydrofuran at -78 - -20℃; for 72 h; | Reference Example 40 Methyl 5-bromo-1H-pyrrole-3-carboxylate A solution (70 mL) of methyl 1H-pyrrole-3-carboxylate (4.48 g) in tetrahydrofuran was cooled to -78°C, N-bromosuccinimide (6.30 g) was added, pyridine (5 drops) was added, and the mixture was left standing in a freezer (-20°C) for 3 days. The reaction mixture was concentrated under reduced pressure, water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→1:1) to give the title compound as a pale-yellow solid (yield 3.59 g, 49percent). 1H-NMR (CDCl3)δ: 3.81 (3H, s), 6.58 (1H, m), 7.36 (1H, m), 8.60 (1H, brs). |
38 g | With N-Bromosuccinimide In tetrahydrofuran at -78 - 20℃; | (e) methyl 5-bromo-1 H-pyrrole-3-carboxylate To a solution of compound 71 d (40 g) in THF (60 ml) was added /V-bromosuccinimide (67.6 g) portion wise at -78°C. The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was concentrated. The crude product was purified by chromatography on silica gel, eluting with (Petrol: ethyl acetate=10:1 ) to give the desired compound. Yield: 38 g 1H NMR δ (ppm)(CHCI3-d): 8.625 (br, 1 H), 7.364 (dd, 1 H, Hz J2=2.8 Hz), 6.588 (dd, 1 H, Hz J2=2.4 Hz), 3.808 (s, 3H). |
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