Thiophenol → Diphenyl sulfide

HRID 2217035Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([SH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:2]1([S:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7969Thiophenol

HCID 11575Iodobenzene

Product 1

HCID 8766Diphenyl sulfide

Procedure

The general procedure was used to convert iodobenzene and thiophenol to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a clear oil (360 mg, 98% yield). 1H NMR (300 MHz, CDCl3) δ 7.48–7.44 (m, 4H; Ha, Ha′, Hd, Hd′), 7.42–7.39 (m, 4H; Hb, Hb′, He, He′), 7.37–7.31 (m, 2H; Hc, Hc′). 13C NMR (75 MHz, CDCl3) δ 135.70 (C1), 130.94 (C2), 129.10 (C3), 126.94 (C4). Anal. Calcd. for C12H10S: C, 77.37; H, 5.41; S, 17.21; Found C, 77.50; H, 5.45; S, 17.00.

Sources & evidence

ORD record: ord-43af12036d7d48708a45a49fb2548890
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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