2-Iodotoluene → 2'-Methyl[1,1'-biphenyl]-2-thiol

HRID 2217029Notes

Reaction equation

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

Participants

Reactant 2

HCID 51282-Iodotoluene

HCID 7969Thiophenol

Product 1

HCID 131539832'-Methyl[1,1'-biphenyl]-2-thiol

Procedure

The general procedure was used to convert 2-iodotoluene and thiophenol to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a clear oil (386 mg, 96% yield). 1H NMR (300 MHz, CDCl3) δ 7.20–7.00 (m, 9H; Ha, Hb, Hc, Hd, He, He′, Hf, Hf′, Hg), 2.26 (s, 3H; methyl protons). 13C NMR (75 MHz, CDCl3) δ 139.88 (C8), 136.08 (C6), 133.69 (C1), 132.93 (C2), 130.54 (C5), 129.55 (C9, C13), 129.07, (C10, C12), 127.84 (C3), 126.66 (C11), 126.27 (C4), 20.55 (C7). Anal. Calcd. for C13H12S: C, 77.95; H, 6.04; S, 16.01; Found C, 77.87; H, 6.06; S, 15.81.

Sources & evidence

ORD record: ord-453a99a31a8245a6b24c435aab284198
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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