Bromocyclopentane → 1-bromo-3-(cyclopentyloxy)benzene

HRID 2360426Notes

Reaction equation

HRID 2360426 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.[CH:15]1(Br)[CH2:19][CH2:18][CH2:17][CH2:16]1>C(#N)C>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:9]=1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 189804801-bromo-3-(cyclopentyloxy)benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (400 mg, 2.8 mmol) was added to 3-Bromophenol (500 mg, 2.8 mmol) dissolved in acetonitrile and the mixture was refluxed for 1 h and cooled to RT. cyclopentyl bromide (430 mg, 2.8 mmol) was added and the mixture refluxed again overnight. Work up (H2O/EtOAc) and purification afforded the title compound as a pale-yellow liquid. 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.11 (t, J 8.3, 1H), 7.05-7.00 (m, 2H), 6.82-6.76 (m, 1H), 4.76-4.68 (m, 1H), 1.94-1.73 (m, 6H), 1.65-1.54 (m, 2H).

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. temperaturethe mixture refluxed again overnight
  3. custom(H2O/EtOAc) and purification

Sources & evidence

ORD record
ord-7955e892088a4cb4a3a6e54b79fec159
Source dataset
uspto-grants-2014_04
Patent number
US08686048B2

Reaction notes

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