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. The resulting mixture was cooled to −10° C., and bromoacetyl bromide (500 g) was added dropwise thereto, followed by stirring the resulting mixture at a temperature between 10° C. and 0° C. for 2 hours. After completion of the reaction, the organic layer was sequentially washed with hydrochloric acid, aqueous sodium bicarbonate and with brine, and dried over magnesium sulfate, followed by evaporation under reduced pressure to obtain 678 g of 2-bromo-N-(2,2,3,3,3-pentafluoropropyl)acetamide as white powder.
Workup
- customAfter completion of the reaction
- washthe organic layer was sequentially washed with hydrochloric acid, aqueous sodium bicarbonate and with brine
- dry with materialdried over magnesium sulfate
- customfollowed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-aba34f7418e54f4386bc2dd96576b927
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173824B2
Reaction notes
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