Ethyl 4-bromobutyrate → Ethyl 4-phenoxybutanoate

Reaction equation

[O:1]1CCCC(=O)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.Br[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[O:1]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:3]=1

Participants

Reactant 2

HCID 76300Ethyl 4-bromobutyrate

HCID 3155752,3,4,5-Tetrahydro-1-benzoxepin-5-one

Product 1

HCID 222539Ethyl 4-phenoxybutanoate

Procedure

Scheme 1 shows a general method for preparation of 3,4-dihydrobenzo[b]oxepin-5(2H)-one intermediates 66 by O-alkylation of a phenolic compound with ethyl 4-bromobutanoate to give a ethyl 4-phenoxybutanoate intermediate 67, followed by saponification to the carboxylic acid 68 and intramolecular cyclization under acidic conditions.

Sources & evidence

ORD record: ord-3f79208ddd564cc696278045e61effac
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846762B2

Reaction notes

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