Triethylamine → (Z)-2-bromo-3-cyclopentyl-acrylic acid ethyl ester

Reaction equation

[CH2:1]([O:3][C:4](=[O:12])/[CH:5]=[CH:6]/[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:2].[Br:13]Br.C(N(CC)CC)C>>[CH2:1]([O:3][C:4](=[O:12])/[C:5](/[Br:13])=[CH:6]/[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:2]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 24408Bromine

HCID 11182849(E)-ethyl 3-cyclopentylacrylate

Product 1

HCID 86605124(Z)-2-bromo-3-cyclopentyl-acrylic acid ethyl esterYield 65%

Procedure

Following the method of example 54b, reaction of (E)-3-cyclopentyl-acrylic acid ethyl ester (87 g, 520 mmol) with bromine (29.3 ml, 572 mmol) and triethylamine (90 ml, 650 mmol) affords the title product as an oil (83.5 g) GC-MS (m/e): 247 (M+).

Sources & evidence

ORD record: ord-478f92a3f8334cf5a8d37fdddb0a2542
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576108B2

Reaction notes

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