[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[F:7][C:8]1[CH:9]=[C:10]([CH:15]2[CH2:17][O:16]2)[CH:11]=[CH:12][C:13]=1[F:14].C(OCC)(=O)C.CCCCCC>CO.O>[N:1]([CH2:17][CH:15]([C:10]1[CH:11]=[CH:12][C:13]([F:14])=[C:8]([F:7])[CH:9]=1)[OH:16])=[N+:2]=[N-:3]Sodium azide (625 mg, 9.6 mmol) followed by ammonium chloride (514 mg, 9.6 mmol) were added to a solution of 2-(3,4-difluorophenyl)oxirane (1 g, 6.4 mmol) in methanol (10 mL) and water (2.5 mL). After stirring at 80° C. overnight, the reaction mixture was concentrated to give a residue. The residue was partitioned between water and ethyl acetate. The organic phase was washed with brine, dried (sodium sulfate) and concentrated to give a residue. Chromatography of the residue over silica gel eluting with 10-50% ethyl acetate/hexane afforded 2-azido-1-(3,4-difluorophenyl)ethanol.
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