5-Bromo-2-(trifluoromethoxy)aniline synthesis

Yield:886762-08-9 70%

Reaction Conditions:

with iron;acetic acid at 0 - 20; for 2 h;

Steps:

58.1 5-bromo-2-(trifluoromethoxy)aniline (1):
5-bromo-2-(trifluoromethoxy)aniline (1): To a solution of 4-bromo-2-nitro-l- (trifluoromethoxy)benzene (2.0 g, 7.0 mmol) in acetic acid (10.0 mL) was added Fe -powder (1.0 g, 17.9 mmol) at 0-10 °C. The reaction mixture was allowed to stir at room temperature for 2 h. After completion of the reaction, acetic acid was distilled and the residue was diluted with water, basified with saturated sodium bicarbonate solution and extracted with ethyl acetate (2x50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 1 (1.2g, 70%) as a brown gummy solid. 1H NMR (400 MHz, DMSO- d₆): δ 5.68 (s, 2H), 6.65-6.66 (dd, J = 2.4 Hz, 6.2 Hz, 1H), 6.95-6.96 (d, J = 2.5 Hz, 1H), 7.01- 7.01 (dd, J = 1.4 Hz, 8.6 Hz, 1H). MS m/z (M+H): 256.3.

References:

CELGENE AVILOMICS RESEARCH, INC.;ALEXANDER, Matthew David;MCDONALD, Joseph John;NI, Yike;NIU, Deqiang;PETTER, Russell C.;QIAO, Lixin;SINGH, Juswinder;WANG, Tao;ZHU, Zhendong WO2014/149164, 2014, A1 Location in patent:Paragraph 00758; 00892

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