1-Bromo-4-iodobenzene → Ethyl (4-bromophenyl)(difluoro)acetate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:17])[C:13](Br)([F:15])[F:14])[CH3:10]>[Cu].CS(C)=O>[CH2:9]([O:11][C:12](=[O:17])[C:13]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)([F:15])[F:14])[CH3:10]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 55 °C
Procedure
According to the Kumadaki method (supra) and the above-described scheme, 4-bromoiodobenzene (848.7 mg, 3.0 mmol), bromodifluoroacetic acid ethyl ester (Compound 1f; 608.9 mg, 3.0 mmol), copper powder (381 mg, 6.0 mmol) and DMSO (6.0 mL) were put into a two-neck reaction tube, and the mixture was stirred under argon atmosphere at 55° C. for 24 hours. The reaction mixture was extracted with ethyl acetate and washed with water, and an organic layer was dried with anhydrous sodium sulfate. Ethyl acetate was distilled away under reduced pressure, and by carrying out purification by silica gel column chromatography, 2-(4-bromophenyl)-2,2-difluoroacetic acid ethyl ester (Compound 2f) was obtained with a yield of 69%.
Workup
- extractionThe reaction mixture was extracted with ethyl acetate
- washwashed with water
- dry with materialan organic layer was dried with anhydrous sodium sulfate
- distillationEthyl acetate was distilled away under reduced pressure
- custompurification by silica gel column chromatography
Sources & evidence
- ORD record
- ord-cb8277a80ab741ecb27378b02c15de61
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802886B2
Reaction notes
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