Azobisisobutyronitrile → tert-Butyl(2S)-[4-(bromomethyl)phenyl](cyclopentyl)acetate

HRID 877194Notes

Reaction equation

HRID 877194 reaction equation
[CH:1]1([C@@H:6]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:33]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:33][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 54452340tert-Butyl(2S)-cyclopentyl-(4-methylphenyl)acetate

Product 1

HCID 54405806tert-Butyl(2S)-[4-(bromomethyl)phenyl](cyclopentyl)acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.0 g (10.93 mmol) of tert-butyl(2S)-cyclopentyl-(4-methylphenyl)acetate were heated to reflux in 20 ml of chloroform, and 90 mg (0.55 mmol) of 2,2′-azobis(2-methylpropanenitrile) and 2.72 g (15.31 mmol) of N-bromosuccinimide were then added in 5 portions every 30 min. The mixture was stirred under reflux for 6 h and then cooled to RT and concentrated on a rotary evaporator. The residue was purified by chromatography on 120 ml of silica gel (mobile phase cyclohexane/ethyl acetate 4:1). This gave 2.8 g (72% of theory) of the title compound.

Workup

  1. temperatureunder reflux for 6 h
  2. concentrationconcentrated on a rotary evaporator
  3. customThe residue was purified by chromatography on 120 ml of silica gel (mobile phase cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-800d067a0697433a8ddd447207de30b1
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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