Azobisisobutyronitrile → Ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate

HRID 877203Notes

Reaction equation

HRID 877203 reaction equation
[F:1][C:2]([F:19])([F:18])[CH:3]([CH3:17])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC(Cl)Cl>[Br:20][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH:4]([CH:3]([CH3:17])[C:2]([F:18])([F:19])[F:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 58136599Ethyl 4,4,4-trifluoro-3-methyl-2-(4-methylphenyl)butanoate

Product 1

HCID 58136537Ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.25 g (8.2 mmol) of ethyl 4,4,4-trifluoro-3-methyl-2-(4-methylphenyl)butanoate, 1.53 g (8.6 mmol) of N-bromosuccinimide and 67 mg (0.41 mmol) of 2,2′-azobis(2-methylpropanenitrile) in 36 ml of trichloromethane were stirred under reflux overnight. 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 40:1). This gave 2.667 g (7.5 mmol, 92% of theory) of a yellowish oil.

Workup

  1. temperatureunder reflux overnight
  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 40:1)

Sources & evidence

ORD record
ord-12685eaf90d44783ac63cf6a7781e548
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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