Benzyl mercaptan → HCID 70869237, compound

HRID 1844690Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([Br:12])[CH:3]=1.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:64]1([CH2:70][SH:71])[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=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]>[CH2:70]([S:71][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([Br:12])[CH:3]=1)[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1,3-Dibromo-5-tert-butylbenzene (2.89 g, 10 mmol) in dioxane (160 mL) was stirred under Ar. Then DIPEA (3.09 mL, 16 mmol), Xantphos (0.28 g, 0.48 mmol) and Pd2(dba)3 (0.24 g, 0.24 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (0.94 mL, 8 mmol) was slowly added and the reaction was stirred for 6 h, quenched by the addition of H2O (15 mL) and extracted with EA (3×). The combined organic layers were washed with water, dried over Na2SO4, filtered, evaporated and purified by CC to afford compound P21a (1.7 g, 72%).

Workup

customquenched by the addition of H2O (15 mL)
extractionextracted with EA (3×)
washThe combined organic layers were washed with water
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
custompurified by CC
customto afford compound P21a (1.7 g, 72%)

Sources & evidence

ORD record: ord-babdd89793a4410387e37ac28545c0a1
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946446B2

Reaction notes

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