(4E)-3-(4-chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexenyl phenyl sulfoxide → 1-[(2E)-4-(4-chlorophenyl)-2,3-difluoro-2,5-hexadienyl]-3-phenoxybenzene

HRID 1634383Notes

Reaction equation

C1(S([CH2:9][CH2:10][CH:11]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)/[C:12](/[F:29])=[C:13](\[F:28])/[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)=O)C=CC=CC=1>ClC1C=CC=CC=1Cl>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([CH:11]([CH:10]=[CH2:9])/[C:12](/[F:29])=[C:13](\[F:28])/[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of (4E)-3-(4-chlorophenyl)-4,5-difluoro-6-(3-phenoxyphenyl)-4-hexenyl phenyl sulfoxide (0.318 g, 0.60 mmol) in o-dichlorobenzene (2.4 ml) under nitrogen was heated at 165° C. for 4.5 hours. The solution was cooled to 100° C. and the solvent removed in vacuo. The residue was chromatographed on a preparative thin layer silica gel plate eluting with ethyl acetate:hexane (5:95) to yield the title compound as a pale yellow oil (0.142 g) which was characterized by IR, 1HNMR and mass spectral analysis.

Workup

customthe solvent removed in vacuo
customThe residue was chromatographed on a preparative thin layer silica gel plate
washeluting with ethyl acetate:hexane (5:95)

Sources & evidence

ORD record: ord-558c4e84a0ce43c79913032cedbdf727
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506800B2

Reaction notes

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