Water → ({3-[(5-Bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine

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Reaction Steps

1-(azidomethyl)-3-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorobenzene (8.3 g, 20.29 mmol) dissolved in THF (100 mL) was treated successively with triphenylphosphine (7.98 g, 30.4 mmol) and water (1.828 g, 101 mmol) at 25° C. for 2 days with stirring. The reaction mixture was concentrated to dryness and purified on 330 g silica gel eluted successively with EtOAc (to remove triphenylphosphine oxide) followed by 0 to 10% CH3OH/DCM to give ({3-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)amine (5.73 g, 14.96 mmol, 73.7% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.48-7.63 (m, 3H), 6.71 (s, 1H), 3.77 (s, 2H), 1.90 (s, 2H). LC-MS (ES−) m/z 380.00, 381.97, 384.06 [M−1]. LC-MS (ES+) m/z 381.84, 383.83, 385.87 [M+H].

Provenance & Evidence