Iodobenzene → (2,6-Dimethyl-phenyl)-phenyl sulfide

HRID 2217041Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[SH:16]>>[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[S:16][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 11575Iodobenzene

HCID 610452,6-Dimethylthiophenol

Product 1

HCID 13511540(2,6-Dimethyl-phenyl)-phenyl sulfide

Procedure

The general procedure was used to convert iodobenzene and 2,6-dimethylthiophenol to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a clear oil (409 mg, 95% yield). 1H NMR (300 MHz, CDCl3) δ 7.1–6.98 (m, 5H; Hc, Hc, Hd, Hd′, He), 6.93–6.86 (m, 1H; Hb), 6.77 (d, J=7.16, 2H; Ha, Ha′) 2.34 (s, 6H; methyl protons). 13C NMR (75 MHz, CDCl3) δ 143.86 (C2, C6), 137.98 (C9), 130.43 (C1), 129.22 (C4), 128.86 (C10, C14), 128.40 (C1, C13), 125.59 (C3, C5), 124.57 (C12), 21.82 (C7, C8). Anal. Calcd. for C14H14S: C, 78.45; H, 6.58; S, 14.96; Found C, 78.58; H, 6.71; S, 14.98.

Sources & evidence

ORD record: ord-7db4e735b69146b7a9e584cecaaf128e
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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