N,N-Dimethylaniline → 2-bromo-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Reaction equation
[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3][NH2:4].CN(C)C1C=CC=CC=1.[Br:19][CH2:20][C:21](Br)=[O:22]>C(OCC)(=O)C>[Br:19][CH2:20][C:21]([NH:4][CH2:3][C:2]([F:9])([F:1])[C:5]([F:8])([F:7])[F:6])=[O:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
2,2,3,3,3-Pentafluoropropylamine (produced by Synquest) (389 g) was dissolved in ethyl acetate (1.56 L), and N,N-dimethylaniline (316 g) was added thereto. After cooling the mixture to −10° C., bromoacetyl bromide (500 g) was added dropwise thereto, and the resulting mixture was stirred at a temperature between 10° C. and 0° C. for 2 hours. The organic layer was sequentially washed with aqueous hydrochloric acid, aqueous sodium bicarbonate and with brine, and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure to obtain 2-bromo-N-(2,2,3,3,3-pentafluoropropyl)acetamide (678 g) as a white powder.
Workup
- washThe organic layer was sequentially washed with aqueous hydrochloric acid, aqueous sodium bicarbonate and with brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationfollowed by concentration under reduced pressure
Sources & evidence
- ORD record
- ord-1aada4678f73404c993a2f0c0f107ab6
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08212059B2
Reaction notes
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