N-bromobutanimide → Tert-butyl 2-(4-(bromomethyl)phenyl)-3-methylpentanoate

HRID 877150Notes

Reaction equation

HRID 877150 reaction equation
[CH3:1][CH:2]([CH2:18][CH3:19])[CH:3]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[Br:20]N1C(=O)CCC1=O>ClCCl>[Br:20][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH:3]([CH:2]([CH3:1])[CH2:18][CH3:19])[C:4]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:5])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58074556Tert-butyl 3-methyl-2-(4-methylphenyl)pentanoate

Product 1

HCID 58074549Tert-butyl 2-(4-(bromomethyl)phenyl)-3-methylpentanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15 g (59.1 mmol) of tert-butyl 3-methyl-2-(4-methylphenyl)pentanoate, 11 g (62 mmol) of N-bromosuccinimide and 97 mg (0.59 mmol) of 2,2′-azobis-2-methylpropanenitrile in 150 ml of dichloromethane were stirred under reflux for 2 h. After the reaction had gone to completion, the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 20:1). This gave 16.22 g (47.5 mmol, 80% of theory) of a colorless oil.

Workup

  1. temperatureunder reflux for 2 h
  2. customthe solvent was removed under reduced pressure
  3. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-430d5cc787b0411f91d732eb6d0a7bc8
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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