Water → N-(4-Bromobutyl)-2,2,2-trifluoro-N-isopropylacetamide

HRID 253481Notes

Reaction equation

HRID 253481 reaction equation
[H-].[Na+].[F:3][C:4]([F:12])([F:11])[C:5]([NH:7][CH:8]([CH3:10])[CH3:9])=[O:6].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.O>CN(C=O)C>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][N:7]([CH:8]([CH3:10])[CH3:9])[C:5](=[O:6])[C:4]([F:12])([F:11])[F:3]

Participants

6

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 23052532,2,2-Trifluoro-N-isopropylacetamide

Product 1

HCID 86053285N-(4-Bromobutyl)-2,2,2-trifluoro-N-isopropylacetamideYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

21 g (520 mmol) of 60% sodium hydride are suspended in 700 ml of anhydrous DMF under an inert atmosphere, and the mixture is cooled to 0° C. 40.5 g (260 mmol) of 2,2,2-trifluoro-N-isopropylacetamide are slowly added portionwise. After 15 minutes, 62 ml (520 mmol) of 1,4-dibromobutane are added. The reaction medium is then heated at 60° C. for 3 hours, and then cooled to room temperature, poured into 1 L of water and extracted with ethyl acetate. The organic phase is washed with water and dried, and the residue obtained is purified by distillation. A colorless oil is obtained (m=0.18 g, yield=24%).

Workup

  1. temperatureThe reaction medium is then heated at 60° C. for 3 hours
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. customdried
  6. customthe residue obtained
  7. distillationis purified by distillation
  8. customA colorless oil is obtained (m=0.18 g, yield=24%)

Sources & evidence

ORD record
ord-3a38f05933324537af6e6a51d9eeba64
Source dataset
uspto-grants-2011_01
Patent number
US07872026B2

Reaction notes

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