1,4-Dibromobenzene → 1-(4-Bromophenyl)cyclopentan-1-ol

HRID 855326Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:12])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Br[C:14]1C=CC(Br)=CC=1.[Li]CCCC.CCCCCC.C1(=O)CCCC1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([OH:12])[CH2:11][CH2:10][CH2:9][CH2:14]2)=[CH:6][CH:7]=1

Participants

Reactant 5

HCID 78041,4-Dibromobenzene

HCID 8058Hexane

HCID 8452Cyclopentanone

HCID 120954191-(4-Bromophenyl)cyclobutanol

HCID 178418339Butyllithium

Product 1

HCID 231542891-(4-Bromophenyl)cyclopentan-1-olYield 39%

Procedure

The title compound was synthesized in analogy to 1-(4-bromo-phenyl)-cyclobutanol (described in example S97) using 3 g of 1,4-dibromobenzene (12.7 mmol), 7.95 ml of a 1.6 molar solution of n-BuLi in hexane (12.7 mmol) and 1.24 ml of cyclopentanone (14.0 mmol). The isolated residue was purified by flash column chromatography (1:4 diethyl ether/pentane) to give 1.2 g of 1-(4-bromo-phenyl)-cyclopentanol (39%) as a colorless liquid.

Workup

customThe isolated residue was purified by flash column chromatography (1:4 diethyl ether/pentane)

Sources & evidence

ORD record: ord-42bc9c8a4b4b4b8698cd2f51a8ca413c
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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