N,N-Dimethylaniline → 2-bromo-N-(2,2,3,3,3-pentafluoropropyl)acetamide

HRID 1510968Notes

Reaction equation

HRID 1510968 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

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

  1. washThe organic layer was sequentially washed with aqueous hydrochloric acid, aqueous sodium bicarbonate and with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. 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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