4-bromo-2-fluoro-6-methoxyaniline;hydrobromide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 4-bromo-2-fluoro-6-methoxyaniline hydrobromide (1 equiv) in DCM (0.3 M) was added boron tribromide (2 equiv) in DCM at 0° C. The reaction mixture was stirred at room temperature for 2 h. After quenching, the reaction mixture was diluted with DCM then purified by silica gel chromatography (0 to 100% ethyl acetate in hexane) to give the title compound (92% yield). MS (ESI) m/z 205.9 [M+H]+. After quenching the reaction mixture was diluted with DCM then purified by silica gel chromatography (0 to 100% ethyl acetate in hexane)

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-fluoro-6-methoxyaniline (1 equiv) in acetic acid (0.7 M) was cooled to 5° C. A mixture of bromine (0.9 equiv) in acetic acid (0.7 M) was slowly added. The reaction mixture was stirred for 2 h at 5° C. The resulting solid was filtered, washed with ether, and dried to give the title compound (90% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 3.84 (s, 3H) 6.79 (br. s., 2H) 6.97 (s, 1H) 7.06 (d, J=10.09 Hz, 1H). MS (ESI) m/z 219.9 [M+H]+. was slowly added The resulting solid was filtered washed with ether dried