N-bromobutanimide → Tert-butyl 2-[4-(bromomethyl)phenyl]-5,5,5-trifluoropentanoate

HRID 238174Notes

Reaction equation

HRID 238174 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][CH2:4][CH:5]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH:5]([CH2:4][CH2:3][C:2]([F:20])([F:21])[F:1])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58074515Tert-butyl 5,5,5-trifluoro-2-(4-methylphenyl)pentanoate

Product 1

HCID 58074495Tert-butyl 2-[4-(bromomethyl)phenyl]-5,5,5-trifluoropentanoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

540 mg (1.79 mmol) of tert-butyl 5,5,5-trifluoro-2-(4-methylphenyl)pentanoate, 333.8 mg (1.78 mmol) of N-bromosuccinimide and 14.7 mg (0.09 mmol) of 2,2′-azobis-2-methylpropionitrile in 10 ml of carbon tetrachloride were stirred under reflux for 2 h. After the reaction had gone to completion, the succinimide was filtered off and the filter residue was washed with dichloromethane. The filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 659 mg (1.72 mmol, 97% of theory) of a yellowish oil.

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationthe succinimide was filtered off
  3. washthe filter residue was washed with dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-22d16ef908434f6581ad8bedbcda2d1d
Source dataset
uspto-grants-2014_02
Patent number
US08642592B2

Reaction notes

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