1-Bromo-5-methyl-2-nitro-4-(trifluoromethyl)benzene synthesis

Yield:871571-25-4 77%

Reaction Conditions:

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

Steps:

A.4.2

Step 2: 1-Bromo-5-methyl-2-nitro-4-trifluoromethyl-benzene To a rapidly stirred mixture of tert-butyl nitrite (45.33 mL, 382 mmol) and copper(II) bromide (76.1 g, 341 mmol) in acetonitrile (450 mL) at 65° C. was added cautiously solid 5-methyl-2-nitro-4-trifluoromethyl-phenylamine from step 1 (50.0 g, 227 mmol). After the addition was complete, stirring was continued for further 1 h at 65° C. The mixture was cooled to 23° C. and poured into 1 N HCl (1000 mL), extracted twice with TBME, the organic layer was washed with brine, dried over MgSO₄. Removal of the solvent in vacuum left a brown oil, which was purified by silica gel column chromatography with heptane/ethyl acetate 9:1 to give the title compound as a yellow liquid (49.8 g, 77%). MS (EI) 283.0 [M] and 285.0 [M⁺2].

References:

US2006/183756,2006,A1 Location in patent:Page/Page column 10