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851045-64-2

4-methyl-3-(trifluoromethoxy)aniline synthesis

2synthesis methods
-

Yield:851045-64-2 79%

Reaction Conditions:

with cesium fluoride;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,4-dioxane at 80; for 3 h;

Steps:

182.2

Step 2. Preparation of 4-methyl-3-trifluoromethoxyanaline. Add 1, 1-bis (diphenylphosphino) ferrocene palladium (II) chloride (0.8 g, 0.1 mmol), methyl boronic acid (1.8 g, 29.7 mmol) and cesium fluoride (5.2 g, 34.6 mmol) to a solution of 4-iodo-3-trifluoromethoxyanaline (3.0 g, 9.9 mmol) in dioxane under nitrogen. After heating at 80 °C for 3 h, cool the reaction to room temperature and dilute with ethyl acetate (100 mL) and water (100 mL). Separate the organics, wash with brine, dry over sodium sulfate, and filter. Remove the solvent under vacuum and chromatograph the crude product over silica gel using ethyl acetate/hexane (5-20%) to elute. This provides the title compound (1.5 g, 79 %) as a tan oil: MS (ES+): 192 (M+H).

References:

WO2005/37796,2005,A1 Location in patent:Page/Page column 151