4-Methylbenzenethiol → HCID 67183685, compound

HRID 2217036Notes

Reaction equation

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

Participants

Reactant 2

HCID 78114-Methylbenzenethiol

HCID 11575Iodobenzene

Product 1

HCID 67183685HCID 67183685, compound

Procedure

The general procedure was used to convert iodobenzene and p-toluenethiol to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a clear oil (388 mg, 97.0% yield). 1H NMR (300 MHz, CDCl3) δ 7.18 (dt, J=8.1, 2H; Ha, Ha′), 7.15–7.12 (m, 4H; He, He′, Hf, Hf′), 7.08 (m, 1H; Hg), 7.04–7.00 (d, J=7.34, 2H; Hc, Hc′), 2.22 (s, 3H; methyl protons). 13C NMR (75 MHz, CDCl3) δ 138.05 (C4), 137.62 (C1′), 132.77 (C2, C6), 131.76 (C1), 130.55 (C3, C5), 130.23 (C2′, C6′), 129.52 (C3′, C5′), 126.87 (C4′), 21.62 (C7). Anal. Calcd. for C13H12S: C, 77.95; H, 6.04; S, 16.01; Found C, 77.78; H, 6.01; S, 16.19.

Sources & evidence

ORD record: ord-3429b94c10454299ab4f677ecf2ebdf2
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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