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CAS No. : | 812667-44-0 | MDL No. : | MFCD12913570 |
Formula : | C8H8BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 230.06 | Pubchem ID : | - |
Synonyms : |
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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 |
---|---|---|
92% | With trifluorormethanesulfonic acid; triethylamine In dichloromethane at 0 - 20℃; for 1.5 h; | To a solution of 9.22g (40.1mmol) of the compound obtained in the Manufacturing Example 1 in 200mL of anhydrous dichloromethane were added 11.17mL (80.2mmol) of triethyamine and 8.09mL of anhydrous trifluoromethanesulfonic acid at 0°C, and the mixture was stirred for 30 minutes at the same temperature and for 1 hour at room temperature. Then, water was added to the reaction mixture and the mixture was extracted with dichloromethane. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: chloroform) to give 7.84g (92percent) of the title compound. |
53% | Stage #1: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.25 h; Stage #2: With O-phenyl phosphorodichloridate In dichloromethane at 0 - 20℃; for 1.2 h; |
[00198] Step 2: A solution of 4-bromo-2-methoxybenzamide (508 mg, 2.21 mmol) in anhydrous DCM (10 mL) was cooled to 0 0C and then treated with 1,8- diazabicyclo(5.4.0)undec-7-ene (0.991 mL, 6.62 mmol). The mixture was stirred at 0 0C for 15 min, and then treated with phenyl dichlorophosphate (0.660 mL, 4.42 mmol) over 2 min. The reaction was stirred at 0 0C for 10 min, and then warmed to RT where it stirred for 1 h. After this time, the mixture was partitioned betweenDCM (10 mL) and saturated NH4Cl (20 mL). The aqueous phase was extracted with DCM. The combined extracts were dried (MgSO4) and concentrated to give the crude product, which was purified by flash chromatography (12 g SiO2 column; 0- 30percent EtO Ac/Hex gradient) to give 4-bromo-2-methoxybenzonitrile (250 mg, 1.18 mmol, 53 percent yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ ppm 7.40 (1 H, s), 7.16 (1 H, s), 7.12 (1 H, s), 3.91 (3 H, s). |
53% | Stage #1: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.25 h; Stage #2: With O-phenyl phosphorodichloridate In dichloromethane at 0 - 20℃; for 1.2 h; |
[00198] Step 2: A solution of 4-bromo-2-methoxybenzamide (508 mg, 2.21 mmol) in anhydrous DCM (10 mL) was cooled to 0 0C and then treated with 1,8- diazabicyclo(5.4.0)undec-7-ene (0.991 mL, 6.62 mmol). The mixture was stirred at 0 0C for 15 min, and then treated with phenyl dichlorophosphate (0.660 mL, 4.42 mmol) over 2 min. The reaction was stirred at 0 0C for 10 min, and then warmed to RT where it stirred for 1 h. After this time, the mixture was partitioned betweenDCM (10 mL) and saturated NH4Cl (20 mL). The aqueous phase was extracted with DCM. The combined extracts were dried (MgSO4) and concentrated to give the crude product, which was purified by flash chromatography (12 g SiO2 column; 0- 30percent EtO Ac/Hex gradient) to give 4-bromo-2-methoxybenzonitrile (250 mg, 1.18 mmol, 53 percent yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ ppm 7.40 (1 H, s), 7.16 (1 H, s), 7.12 (1 H, s), 3.91 (3 H, s). |