Allyl bromide → Allyl(4-methylphenyl) sulfide

HRID 2413331Notes

Reaction equation

HRID 2413331 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[C:5]1([CH3:16])[CH:10]=[CH:9][C:8]([S:11][Si](C)(C)C)=[CH:7][CH:6]=1>C(#N)C.CN(C)P(=O)(N(C)C)N(C)C>[C:5]1([CH3:16])[CH:10]=[CH:9][C:8]([S:11][CH2:3][CH:2]=[CH2:1])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 7841Allyl bromideHCID 11095572Silane, trimethyl[(4-methylphenyl)thio]-

Product 1

HCID 232029Allyl(4-methylphenyl) sulfideYield 85%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

5.1 ml (59 mmoles) of allyl bromide were added to a mixture of 10.04 g (51.2 mmoles) of p-tolylthio(trimethyl)silane in 20 ml of acetonitrile and 18 ml of hexamethylphosphoric triamide and the conversion was complete after stirring for 20 minutes at room temperature. The reaction mixture was treated as described in Example 3 to obtain 7.1 g (85% yield) of allyl p-tolyl sulfide boiling at 110°-111° C./14 mm Hg and having a refractive index of nD25 =1.5644.

Workup

  1. additionThe reaction mixture was treated

Sources & evidence

ORD record
ord-0983db5433f64ec28272cbfab33d2e66
Source dataset
uspto-grants-1985_01
Patent number
US04496720

Reaction notes

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