Benzoyl chloride, 2-chloro-5-nitro- → (4-Bromo-2-chloro-phenyl)-(2-chloro-5-nitro-phenyl)-methanone

Participants

Reaction Conditions

Reaction Steps

The reaction was run under an argon atmosphere using dry glassware. 4-Bromo-2-chloro-iodobenzene (5.00 g, 15.8 mmol) was dissolved in dry THF (25 mL) and cooled to −35° C. Isopropylmagnesium chloride (2 M in THF, 8.27 mL, 16.5 mmol) was added under stirring during 90 minutes. A solution of ZnCl2 (2.17 g, 15.9 mmol) in dry THF (35 mL) was slowly added to the reaction mixture at −35° C. The reaction mixture was allowed to come to RT after 1 h and a solution of 2-chloro-5-nitro-benzoyl chloride (3.64 g, 16.5 mmol) in THF (45 mL) was added followed by Cu(OAc)2.H2O (63 mg, 0.32 mmol). The resulting reaction mixture was stirred at RT for 18 h. The reaction mixture was poured into a mixture of EtOAc/water/HCl (1N). The organic phase was washed with water, brine and then dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The crude product was purified by flash chromatography using DCM/petroleum ether (40-60) 1:6; 1:4 and 1:2 as the eluent to afford the title compound as yellow solid.

Provenance & Evidence