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 into a 500 ml three-necked flask equipped with Dean-Stark apparatus and a condenser, under an inert atmosphere. 90 ml of DMF and 110 ml of toluene are added. The medium is heated to 140° C. under nitrogen and 80 ml of toluene are distilled off. The medium is then cooled to RT and then deoxygenated by sparging with nitrogen. 6 g of iodoanisole are then added, followed by heating at 155° C. for 20 hours. After cooling to RT, the medium is diluted with 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 Dean-Stark apparatus and a condenser, under an inert atmosphere
- distillation80 ml of toluene are distilled off
- temperatureThe medium is then cooled to RT
- customdeoxygenated
- customby sparging with nitrogen
- addition6 g of iodoanisole are then added
- temperatureby heating at 155° C. for 20 hours
- temperatureAfter cooling to RT
- additionthe medium is diluted with 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-fe3059a5e2924c2891b8309964868356
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504511B2
Reaction notes
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