3,4-Difluorobenzoyl chloride → 3,3',4,4'-Tetrafluorobenzophenone
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](Cl)=[O:6]>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([C:5]([C:8]2[CH:4]=[CH:3][C:2]([F:1])=[C:10]([F:11])[CH:9]=2)=[O:6])[CH:8]=[CH:9][C:10]=1[F:11]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 3,4-difluorobenzoyl chloride (2.206 g, 12.5 mmol) in ethyl ether (20 mL) was cooled to 0° C. and treated with the crude mixture from Example 31 (25 mmol). The reaction was stirred at 0° C. (3 h) and quenched with aqueous ammonium chloride solution. The resulting mixture was stirred at room temperature overnight. The aqueous layer was extracted with two additional portions of ethyl ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Flash chromatography on silica gel (5% EtOAc/hexane) afforded the title compound (28).
Workup
- customquenched with aqueous ammonium chloride solution
- stirringThe resulting mixture was stirred at room temperature overnight
- extractionThe aqueous layer was extracted with two additional portions of ethyl ether
- washthe combined organic extracts were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-aeb8a2738d57490786b70ba283163fdb
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06274583B1
Reaction notes
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