Benzyl mercaptan → Benzyl(3-bromo-2-methylphenyl)sulfane

Participants

Role	Name	HCID	Charge
Reactant	Benzyl mercaptan	HCID 7509	—
Reactant	2,6-Dibromotoluene	HCID 34681	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Benzyl(3-bromo-2-methylphenyl)sulfane	HCID 66911186	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

2,6-dibromotoluene (20 g, 100 mmol) in dioxane (160 ml) was stirred under argon. Then, DIPEA (30.9 ml, 160 mmol), xantphos (2.77 g, 4.8 mmol) and Pd2(dba)3 (2.4 g, 2.4 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (9.4 ml, 80 mmol) was slowly added and the reaction stirred for 6 h. The reaction was quenched by the addition of 150 ml of H2O. After extraction (three times) with ethyl acetate, the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08378092B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-fd0db779b5694582a9c0f17d04f568c4
Source note	uspto-grants-2013_02