Iodobenzene → HCID 11148597, compound

HRID 2217040Notes

Reaction equation

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

Participants

Reactant 2

HCID 11575Iodobenzene

HCID 1175483,5-Dimethylbenzenethiol

Product 1

HCID 11148597HCID 11148597, compound

Procedure

The general procedure was used to convert iodobenzene and 3,5-dimethylthiophenol to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a clear oil (417 mg, 97% yield). 1H NMR (300 MHz, CDCl3) δ 7.17–7.01 (m, 5H; Hc, Hc′, Hd, Hd′, He), 6.84 (s, 2H; Ha, Ha′), 6.72 (s, 1H; Hb), 2.10 (s, 3H; methyl protons). 13C NMR (75 MHz, CDCl3) δ 138.81 (C3, C5), 136.35 (C9), 134.69 (C1), 130.44 (C10, C14), 129.10 (C11, C13), 129.02 (C2, C6), 128.68 (C4), 126.61 (C12), 21.13 (C7, C8). Anal. Calcd. for C14H14S: C, 78.45; H, 6.58; S, 14.96; Found C, 78.53; H, 6.62; S, 14.89.

Sources & evidence

ORD record: ord-c1315707bfcb4198ad7c76dfd114df1c
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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