Iodobenzene → 7570-92-5

HRID 2217049Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]1([SH:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:2]1([S:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

Reactant 2

HCID 11575Iodobenzene

HCID 15290Cyclohexanethiol

Product 1

HCID 5734667570-92-5

Procedure

The general procedure was used to convert iodobenzene and cyclohexylmercaptan to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a clear oil (297 mg, 77% yield). 1H NMR (300 MHz, CDCl3) δ 7.44 (dd, J=6.97, 2H; Ha, Ha′), 7.35–7.22 (m, 3H; Hb, Hb′, Hc,), 3.19–3.11 (m, 1H; Hd), 2.04 (m, 2H; He, Hi), 1.82 (m, 2H; He′, Hi′), 1.65 (m, 1H; Hg), 1.48–1.26 (m, 5H; Hh, Hf, Hh′, Hf′, Hg′). 13C NMR (75 MHz, CDCl3) δ 135.11 (C1), 131.75 (C3, C5), 128.64 (C2, C6), 126.46 (C4), 46.44 (C7), 33.26 (C8, C12), 25.97 (C10), 25.69 (C9, C11). Anal. Calcd. for C12H16S: C, 74.94; H, 8.39; S, 16.67; Found C, 75.06; H, 8.40; S, 16.54.

Sources & evidence

ORD record: ord-18455c212afb4bc6a883ec79b0578408
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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