Thiophenol → 1-methoxy-2-(phenylthio)benzene

HRID 2217031Notes

Reaction equation

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

Participants

Reactant 2

HCID 7969Thiophenol

HCID 68257o-Iodoanisole

Product 1

HCID 6414471-methoxy-2-(phenylthio)benzene

Procedure

The general procedure was used to convert 2-iodoanisole and thiophenol to the title product. Purification by flash chromatography (hexane/CH2Cl2 [3:1] as the eluent) gave the analytically pure product as a clear oil (412 mg, 95% yield). 1H NMR (300 MHz, CDCl3) δ 7.41–7.25 (m, 6H; Hc, He, He′, Hf, Hf′, Hg), 7.12 (dd, J=6.03, 1H; Ha), 6.96–6.89 (m, 2H; Hb, Hd), 3.90 (s, 3H; methyl protons). 13C NMR (75 MHz, CDCl3) δ 157.21 (C6), 134.39 (C8), 131.50 (C2), 131.35 (C9, C13), 129.07 (C10, C12), 128.27 (C4), 126.99 (C11), 123.96 (C1), 121.16 (C3), 110.76 (C5), 55.78 (C7). Anal. Calcd. for C13H12OS: C, 72.19; H, 5.59; S, 14.82; Found C, 72.23; H, 5.70; S, 14.67.

Sources & evidence

ORD record: ord-8f61f6988eb44d7e9e22ecb4e53a4341
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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