Triethylsilane → 1-Bromo-4-cyclopentylbenzene

HRID 855327Notes

Reaction equation

HRID 855327 reaction equation
BrC1C=CC(C2CCC2)=CC=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2(O)[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.C([SiH](CC)CC)C>>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 12052TriethylsilaneHCID 231542891-(4-Bromophenyl)cyclopentan-1-olHCID 571850921-Bromo-4-cyclobutylbenzene

Product 1

HCID 543241331-Bromo-4-cyclopentylbenzene

Procedure

The title compound was synthesized in analogy to bromo-4-cyclobutyl-benzene (described in example S113) using 823 mg of 1-(4-bromo-phenyl)-cyclopentanol (3.41 mmol), 652 μl of triethylsilane (4.10 mmol) and 649 μl of boron trifluoride diethyl etherate complex (5.12 mmol). The isolated residue was purified by flash column chromatography (1:9 EtOAc/-cyclohexane) to give 727 mg of a mixture of the desired 4-cyclopentyl-benzene and 1-bromo-4-cyclopent-1-enyl-benzene as a white semi-solid. This mixture was used in the following step without further purification.

Workup

  1. customThe isolated residue was purified by flash column chromatography (1:9 EtOAc/-cyclohexane)

Sources & evidence

ORD record
ord-f370b2120c404b3788ef48ab51ac9077
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

Loading…