Thionyl Chloride → 2-Chloro-4-fluoro-1,3-benzoxazole

HRID 598512Notes

Reaction equation

HRID 598512 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]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178505601HCID 178505601, compound

Product 1

HCID 189668762-Chloro-4-fluoro-1,3-benzoxazoleYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customdry at room temperature
  2. customThe solvent was removed in vacuo
  3. customThe crude compound was purified with flash column chromatography on silica eluting with a gradient
  4. 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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