Water → 1-Bromo-4,5-difluoro-2-(trifluoromethoxy)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[OH:10].[F:11][C:12]([F:16])([F:15])CI.[F-].[Cs+].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[O:10][C:12]([F:16])([F:15])[F:11]Participants
6
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 2-bromo-4,5-difluoro-phenol (1.0 g, 4.8 mmol), 1,1,1-trifluoro-2-iodo-ethane (706 mg, 7.2 mmol) and CsF (882 mg, 5.8 mmol) in DMSO (20 mL) was heated at 120° C. overnight. The reaction mixture was poured into water, and extracted with ethyl acetate (2×). The solvent was removed, and the resulting residue was chromatographed using hexane/ethyl acetate (10:1) to give the title compound (697 mg, 50%). 1H NMR (500 MHz, CDCl3) δ ppm 4.36 (q, J=7.93 Hz, 2H) 6.85 (dd, J=10.98, 7.02 Hz, 1H) 7.43 (t, J=8.85 Hz, 1H).
Workup
- extractionextracted with ethyl acetate (2×)
- customThe solvent was removed
- customthe resulting residue was chromatographed
Sources & evidence
- ORD record
- ord-63159e979ab4479e8ac60afc471ba3a8
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07704997B1
Reaction notes
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