3-Bromo-N-methoxy-N-methylbenzamide → N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2,2-dimethylpropanamide

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Reaction Conditions

Reaction Steps

A flamed dried 500 mL three-necked flask was charged N-(2-bromo-4,5-dimethoxyphenyl)-2,2-dimethylpropanamide (30 g, 95 mmol) and dry THF (200 mL) under N2. n-BuLi (114 mL, 2.5 mol/L, 285 mmol) was added dropwise at −78° C. After the mixture was stirred at −78° C. for 1 hour, 3-bromo-N-methoxy-N-methylbenzamide (23.2 g, 94.9 mmol) in dry THF (30 mL) was added dropwise slowly at −78° C. The resulting mixture was stirred at −78° C. for 3 hours, then quenched with saturated NH4Cl (100 mL). The mixture was exacted with EtOAc (100 mL×3). The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column (30:1 hexanes/ethyl acetate) to afford a N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2,2-dimethylpropanamide as a yellow solid. MS (M+H)=420 and 422.

Provenance & Evidence