Potassium tert-butoxide → 2-Bromo-4-chloro-1-(2-methylenecyclopentyloxy)benzene

HRID 2069615Notes

Reaction equation

[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:9]=1[O:10][CH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[Br:7][C:8]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:9]=1[O:10][CH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[CH2:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To the mixture of methyl triphenylphosphonium bromide (16.0 g, 44.8 mmol) in anhydrous tetrahydrofuran (125 mL) at 0° C. under nitrogen was added portion wise the potassium tert-butoxide (5.0 g, 44.8 mmol). After stirring at 0° C. for 30 minutes, the mixture of 2-(2-bromo-4-chlorophenoxy)cyclopentanone (516B) (10.8 g, 37.3 mmol) in tetrahydrofuran (40 mL) was added slowly. The resulting mixture was stirred at room temperature under nitrogen for 3 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with water, brine, dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5-10% EtOAc in hexanes) to provide 2-bromo-4-chloro-1-(2-methylenecyclopentyloxy)benzene (517) (6.2 g, 58.2%) as a colorless oil.

Workup

additionwas added slowly
stirringThe resulting mixture was stirred at room temperature under nitrogen for 3 hours
customThe reaction mixture was quenched with water
extractionextracted with ethyl acetate
washThe organic phase was washed with water, brine
dry with materialdried with sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography on silica gel (5-10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-ceb96e43aed940f495a079a0ebbd6992
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299117B2

Reaction notes

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