Thiophenol → 1,3,5-Trimethyl-2-(phenylsulfanyl)benzene

HRID 2217034Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1I.[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 7969Thiophenol

HCID 77647Iodomesitylene

Product 1

HCID 123869921,3,5-Trimethyl-2-(phenylsulfanyl)benzene

Procedure

The general procedure was used to convert 2,4,6-trimethyliodobenzene and thiophenol to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a clear oil (444 mg, 97% yield). 1H NMR (300 MHz, CDCl3) δ 7.20 (m, 2H; Hb, Hb′), 7.09 (m, 3H; Hc, Hc′, Hd), 6.96 (m, 2H; Ha, Ha′) 2.44 (s, 6H; ortho methyl protons), 2.37 (s, 3H, para methyl protons). 13C NMR (75 MHz, CDCl3) δ 143.67 (C2, C6), 139.21 (C4), 138.35 (C1), 129.29 (C10), 128.81 (C11, C15), 127.20 (C12, C14), 125.39 (C3, C5), 124.41 (C13), 21.67 (C7, C8), 21.10 (C9). Anal. Calcd. for C15H16S: C, 78.90; H, 7.06; S, 14.04; Found C, 78.76; H, 7.23; S, 14.10.

Sources & evidence

ORD record: ord-df7001255fe345b89072d523573a62b7
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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