1,1-Dibromoethane → HCID 18476046, compound

Participants

Reaction Conditions

Reaction Steps

Zinc dust (14.2 g, 217.2 mmol) and tetrahydrofuran (17 ml) were sonicated under argon for 30 minutes. Dibromoethane (2.1 ml, 24.38 mmol) was added and the mixture heated to 67° C. for 1 minute, cooled to 25° C. and trimethylsilyl chloride (2.5 ml, 19.58 mmol) added. After initial effervescence and exotherm, the mixture was stirred at ambient temperature for 30 minutes. 3M 4-Fluorobenzyl bromide (26 ml, 212 mmol) in tetrahydrofuran (70 ml) was added dropwise with exotherm and stirred at ambient temperature for 1.5 hours. To this a solution of tris(dibenzylideneacetone)palladium(0) (1.3 g, 1.42 mmol) and methyl 2-bromo-5-nitrobenzoate (44 g, 170 mmol) in tetrahydrofuran (550 ml) was added dropwise, under argon, over 30 minutes with exotherm and stirred at ambient for 18 hours. The mixture purified on silica (eluting with ethyl acetate), washed with brine (200 ml) and water (200 ml), dried (magnesium sulphate) and evaporated to give methyl 3-nitro-6-(4-fluorobenzyl)benzoate (65 g) which was used in the next step without further purification.

Provenance & Evidence