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

HRID 2217039Notes

Reaction equation

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

Participants

Reactant 2

HCID 11575Iodobenzene

HCID 23642Thioguaiacol

Product 1

HCID 6414471-methoxy-2-(phenylthio)benzene

Procedure

The general procedure was used to convert iodobenzene and 2-methoxybenzenethiol to the title product. Purification by flash chromatography (hexane/CH2Cl2 [3:1] as the eluent) gave the analytically pure product as a clear oil (406 mg, 94% yield). 1H NMR (300 MHz, CDCl3) δ 7.43–7.25 (m, 6H; Hc, He, He′, HfHf′, Hg), 7.14 (dd, 1H; Ha), 6.96–6.89 (m, 2H; Hb, Hd), 3.90 (s, 3H; methyl protons). 13C NMR (75 MHz, CDCl3) δ 157.20 (C6), 134.38 (C8), 131.88 (C2), 131.35 (C9, C13), 129.15 (C10, C12), 128.25 (C4), 127.40 (C11), 123.93 (C1), 121.14 (C3), 110.75 (C5), 55.76 (C7). Anal. Calcd. for C13H12OS: C, 72.19; H, 5.59; S, 14.82; Found C, 72.22; H, 5.70; S, 14.63.

Sources & evidence

ORD record: ord-537f6885ec6c43e89e2f8fd43c9d4e3e
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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