Benzyl Bromide → 1-(Benzyloxy)-3-ethylbenzene

HRID 1064907Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[CH3:8].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=1)[CH3:8]

Participants

Conditions

Temperature: 2 °C

Procedure

To a suspension of potassium carbonate (17 g, 123 mmol) in N,N-dimethylformamide (40 ml) was added a solution of 3-ethyl-phenol (14.8 ml, 123 mmol) in N,N-dimethylformamide (40 ml) at 2° C. under an argon atmosphere. After stirring for 50 min at 2° C., benzyl bromide (14.6 ml, 123 mmol) was added over a period of 15 min at 2° C. The suspension was stirred for additional 30 min at 2° C. and for 12 h at ambient temperature. After adding ice water (250 ml), the solution was extracted two times with diethyl ether. The combined extracts were washed two times with brine and dried over sodium sulfate. Evaporation of the solvent gave a yellow oil which was purified by column chromatography (silica gel, cyclohexane) to yield 24.3 g (114 mmol, 93%) of the title compound as yellow liquid.

Workup

stirringThe suspension was stirred for additional 30 min at 2° C. and for 12 h at ambient temperature
extractionthe solution was extracted two times with diethyl ether
washThe combined extracts were washed two times with brine
dry with materialdried over sodium sulfate
customEvaporation of the solvent
customgave a yellow oil which
customwas purified by column chromatography (silica gel, cyclohexane)

Sources & evidence

ORD record: ord-8f8b479ccb364d37b4aabde9ad54b9b1
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969725B2

Reaction notes

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