Dibutyl sulfide → HCID 12032193, compound

HRID 2217047Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[I:8].[CH2:9]([S:13]CCCC)[CH2:10][CH2:11][CH3:12]>>[I:8][C:3]1[CH:4]=[CH:5][C:6]([S:13][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:7][CH:2]=1

Participants

Reactant 2

HCID 11002Dibutyl sulfide

HCID 119941,2-Diiodobenzene

Product 1

HCID 12032193HCID 12032193, compound

Procedure

The general procedure was used to convert diiodobenzene and n-butyl sulfide to the title product. Purification by flash chromatography (hexane as the eluent) gave the analytically pure product as a pale yellow oil (512 mg, 88% yield). 1H NMR (300 MHz, CDCl3) δ 7.58–7.55 (d, J=8.4, 2H; Ha, Ha′), 7.05–7.02 (d, J=8.2, 2H; Hb, Hb′), 2.91–2.86 (t, J=7.3, 2H; Hc), 1.67–1.49 (m, 2H; Hd), 1.42–1.30 (m, 2H; He), 0.94–0.89 (t, J=7.3, 3H; methyl protons). 13C NMR (75 MHz, CDCl3) δ 137.6 (C1, C1′), 137.2 (C4), 130.2 (C2, C2′), 90.0 (C3), 32.9 (C5), 30.9 (C6), 21.9 (C7), 13.6 (C8). High Resolution Mass. Spec. for C10H13S; Expected, 291.9783; Found, 291.9796

Sources & evidence

ORD record: ord-e68e76f0b8b94573aa03ead2171ef187
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112697B1

Reaction notes

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