[F:1][C:2]1[CH:3]=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:5]=[C:6]([N+:9]([O-])=O)[C:7]=1[OH:8].O.S(S([O-])=O)([O-])=O.[Na+].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl>O.C(O)C>[NH2:9][C:6]1[CH:5]=[C:4]([C:12]([F:15])([F:13])[F:14])[CH:3]=[C:2]([F:1])[C:7]=1[OH:8]The product from (e) (4.1 g) in water (50 ml) was stirred vigorously while sodium dithionite hydrate (10 g) was added in portions. The mixture was stirred for 30 minutes and then ethanol (25 ml) and further sodium dithionite (5 g) were added. The mixture was stirred for another 15 minutes and then diluted to 400 ml, acidified (HCl) and extracted with dichloromethane (4×200 ml). The dichloromethane extract was dried (MgSO4) and evaporated to give a yellow oil which crystallised on cooling. This was identified as 3-amino-5-fluoro-4-hydroxybenzotrifluoride (2.9 g).
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