Sodium Dithionite → 2-Amino-6-bromo-4-fluorophenol

Reaction equation

S(S([O-])=O)([O-])=O.[Na+].[Na+].[Br:9][C:10]1[C:15]([OH:16])=[C:14]([N+:17]([O-])=O)[CH:13]=[C:12]([F:20])[CH:11]=1>O.C(O)C>[NH2:17][C:14]1[CH:13]=[C:12]([F:20])[CH:11]=[C:10]([Br:9])[C:15]=1[OH:16]

Participants

Procedure

Sodium dithionite (58 g, 335 mmol) was dissolved in warm water (300 mL) and was added slowly to a solution of 6-bromo-4-fluoro-2-nitrophenol (11.8 g, 50 mmol) in 250 mL of ethanol heated on a steam bath. The reaction mixture turned from deep orange to light yellow. The suspension is diluted with water till a clear yellow solution was obtained. Partial concentration on a rotary evaporator induced crystallization. The mixture was then cooled to room temperature and crystals formed. Filtration and drying afforded the title compound as a white solid (5.04 g, 49% yield). MS 207 (M+H)+