Thiophenol → HCID 573666, compound

HRID 1605127Notes

Reaction equation

[C:1]1([S:7]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(S)C=CC=CC=1.C1(Br)CCCC1>>[C:1]1([S:7][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 7969Thiophenol

HCID 8728Bromocyclopentane

HCID 345620(Cyclopentanesulfonyl)benzene

Product 1

HCID 573666HCID 573666, compound

Procedure

The cyclopentyl phenyl sulfone used in this synthesis is also a novel compound. It was initially prepared by reacting benzenethiol with cyclopentyl bromide to form cyclopentyl phenyl sulfide which was in turn oxidized to produce the sulfone. Benzenethiol was reacted with cyclopentyl bromide in the presence of potassium carbonate in an acetone solvent at reflux temperature for 4 hours. The acetone was stripped off, water added, and 30-60 petroleum ether used to extract the sulfide. The ether phase was washed twice with 5 percent sodium hydroxide, once with water, and dried with anhydrous magnesium sulfate. The petroleum ether was then distilled off, leaving a residue which was used in the preparation of the sulfone.

Workup

customIt was initially prepared

Sources & evidence

ORD record: ord-5b9f84d8cdb542a9aaf817df7853fa63
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03949001

Reaction notes

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