Toluene → 1-Methoxy-4-(pentafluoroethyl)benzene
Reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([F:8])([F:7])[C:4]([O-])=O.[K+].CN([CH:15]=[O:16])C.[C:17]1(C)[CH:22]=[CH:21]C=[CH:19][CH:18]=1>[Cu]I>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:4]([C:3]([F:8])([F:7])[C:2]([F:10])([F:9])[F:1])=[CH:19][CH:18]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
8.3 g of potassium pentafluoropropionate and 9.8 g of CuI are introduced, under an inert atmosphere, into a 500 ml three-necked flask equipped with a Dean-Starck apparatus and a condenser. 90 ml of DMF and 110 ml of toluene are added. The medium is heated to 140° C. under nitrogen; 80 ml of toluene are distilled. The medium is then cooled to AT and then deoxygenated with nitrogen bubbling. 6 g of iodoanisole are then added and the medium is heated at 155° C. for 20 h. After a return to AT, the medium is diluted in 200 ml of a water/ethyl ether mixture. The medium is then filtered through Celite®. The organic phase is washed 3 times with water, dried over MgSO4 and then evaporated, to give 4.3 g of a brown oil.
Workup
- customequipped with a Dean-Starck apparatus and a condenser
- distillation80 ml of toluene are distilled
- temperatureThe medium is then cooled to AT
- customdeoxygenated with nitrogen bubbling
- addition6 g of iodoanisole are then added
- temperaturethe medium is heated at 155° C. for 20 h
- additionAfter a return to AT, the medium is diluted in 200 ml of a water/ethyl ether mixture
- filtrationThe medium is then filtered through Celite®
- washThe organic phase is washed 3 times with water
- dry with materialdried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-4b4e220f5296480d90571edb851ea7dc
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767681B2
Reaction notes
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