Thionyl Chloride → 2-Chloro-4-fluoro-1,3-benzoxazole
Reaction equation
[F:1][C:2]1[C:7]2[N:8]=[C:9](S)[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:14])=O>CN(C)C=O>[Cl:14][C:9]1[O:10][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[C:7]=2[N:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 560 mg (3.31 mmol) 4-fluoro-benzooxazole-2-thiol in 3.6 mL (49.65 mmol) thionyl chloride was added dropwise 60.3 □L N,N-dimethylformamide dry at room temperature. The mixture was stirred at room temperature for 2.5 h. The solvent was removed in vacuo. The crude compound was purified with flash column chromatography on silica eluting with a gradient formed from n-heptane and ethyl acetate to provide 434 mg (76.4%) of the title compound as a white solid. MS(m/e): 171 (M+H+).
Workup
- customdry at room temperature
- customThe solvent was removed in vacuo
- customThe crude compound was purified with flash column chromatography on silica eluting with a gradient
- customformed from n-heptane and ethyl acetate
Sources & evidence
- ORD record
- ord-19c1ce3755954d03952a270a6c3038b7
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897627B2
Reaction notes
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