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

HRID 389677

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9].CCN(C(C)C)C(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[C:61]1([CH2:67][SH:68])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:67]([S:68][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

customThe reaction was quenched by the addition of 150 ml of H2O
extractionAfter extraction (three times) with ethyl acetate
washthe combined organic layers were washed with water
dry with materialdried with Na2SO4
customevaporated to dryness
customthe product was purified by silica gel chromatography

Sources & evidence

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

Linked notes

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