1-bromo-5-methoxy-2-nitro-4-(trifluoromethyl)benzene synthesis

Yield:951231-87-1 99%

Reaction Conditions:

with tert.-butylnitrite;copper(ll) bromide in acetonitrile at 65; for 1 h;

Steps:

A.59.2

2) 1-Bromo-5-methoxy-2-nitro-4-trifluoromethyl-benzene: The above prepared 5-methoxy-2-nitro-4-trifluoromethyl-phenylamine (28.9 g, 122 mmol) was portionwise added to a rapidly stirred mixture of tert-butyl nitrite (24.4 mL, 206 mmol) and CuBr₂ (41.0 g, 184 mmol) in MeCN (200 mL) at 65°. After the addition was completed, stirring was continued at 65° C. for 1 h. The reaction mixture was cooled to rt and poured onto 1N HCl (300 mL) extracted twice with TBME, the organic layers were washed with brine, dried over MgSO₄, filtrated and evaporated to get a brown oil, which crystallized to give the 1-bromo-5-methoxy-2-nitro-4-trifluoromethyl-benzene (36.34 g, 99%) as a light brown solid, which was used without further purification.

References:

US2007/232583,2007,A1 Location in patent:Page/Page column 39