Ammonia → 1-(2-Bromo-4-chlorophenyl)ethanamine

関与物質

反応手順

Stir a mixture of 1-(2-bromo-4-chlorophenyl)ethanol (2.33 g, 10 mmol), titanium isopropoxide (6 mL, 20 mmol) and ammonia in ethanol (25 mL, 50 mmol) under N2 at ambient temperature for 6 h. Add sodium tetrahydroborate (0.6 g, 15 mmol) and stir the mixture for 3 h. Quench the reaction with ammonia hydroxide (2 N, 25 mL). Remove the insolubles by filtration. Extract the aqueous layer with ethyl acetate. Combine the organic layers and extract with an HCl solution (1 N, 30 mL). Wash the aqueous layer with ethyl acetate and then treat with a NaOH (2 N) solution to pH 10-12. Extract the aqueous layer with ethyl acetate (50 mL×3). Combine the organic layers and wash with aqueous saturated sodium chloride. Dry over magnesium sulfate. Remove the organic solvent to give the title compound (1.5 g, 64%). MS (ES) m/z 236 [M+1]+.

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