Bromocyclopentane → 1-bromo-3-(cyclopentyloxy)benzene
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 3-bromophenol (commercially available) (1.72 g, 10 mmol), bromocyclopentane (commercially available) (2.96 g, 20 mmol), and K2CO3 (2.56 g, 20 mmol) in acetone (30 mL) was stirred at 80° C. for 18 h. The solvent was removed under reduced pressure and the mixture was extracted with EtOAc (100 mL×2). The combined organic layers was washed with sat NaCl (50 mL), dried over Na2SO4, concentrated, and purified by column to give the title product (1.8 g, yield 75%).
Workup
- customThe solvent was removed under reduced pressure
- extractionthe mixture was extracted with EtOAc (100 mL×2)
- washThe combined organic layers was washed with sat NaCl (50 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- custompurified by column
Sources & evidence
- ORD record
- ord-8a8e81951f3b47faabc830d85e177b3f
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382241B2
Reaction notes
Loading…