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

Temperature

-35 °C

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.

1. customusing dry glassware
2. waitto come to RT after 1 h
3. customThe resulting reaction mixture
4. stirringwas stirred at RT for 18 h
5. washThe organic phase was washed with water, brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give the crude product
10. customThe crude product was purified by flash chromatography

ORD record

ord-51e01a7ace044539b1bbc1a8258ac3bd

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293772B2