Iodobenzene → Benzene, 1-methoxy-4-(phenylthio)-

HRID 2217038Notes

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

Participants

Reactant 2

HCID 11575Iodobenzene

HCID 127654-Methoxybenzenethiol

Product 1

HCID 138547Benzene, 1-methoxy-4-(phenylthio)-

Procedure

The general procedure was used to convert iodobenzene and 4-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 (410 mg, 95% yield). 1H NMR (300 MHz, CDCl3) δ 7.27 (dt, J=8.85, 2H; Ha, Ha′), 7.12–6.96 (m, 5H; HC, Hc′, Hd, Hd′, He), 6.75 (dt, 2H; Hb, Hb′), 3.67 (s, 3H; methyl protons). 13C NMR (75 MHz, CDCl3) δ 159.76 (C4), 138.56 (C8), 135.32 (C2, C6), 128.86 (C9, C13), 128.10 (C10, C12), 125.68 (C11), 124.19 (C1), 114.92 (C3, C5), 55.27 (C7). Anal. Calcd. for C13H12OS: C, 72.19; H, 5.59; S, 14.82; Found C, 72.26; H, 5.59; S, 14.65.

Sources & evidence

ORD record: ord-a9142e5f2d17439d9eff3bfa8d2d2650
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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