Cesium carbonate → [(3-Bromophenyl)imino]dimethyl-lambda6-sulfanone

HRID 876212Notes

Reaction equation

HRID 876212 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[CH3:9][S:10]([CH3:13])(=[NH:12])=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=C3C=2OC2C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=2C3(C)C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([N:12]=[S:10]([CH3:13])([CH3:9])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 123119Sulfoximine, S,S-dimethyl-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 90414134[(3-Bromophenyl)imino]dimethyl-lambda6-sulfanone

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

1-Bromo-3-iodo-benzene (250 μL, 1.96 mmol), (methylsulfonimidoyl)methane (219.188 mg, 2.353 mmol), cesium carbonate (894.466 mg, 2.745 mmol) and dioxane (12 mL) are purged with argon. (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane (85.098, 0.147 mmol) and tris(dibenzylideneacetone)dipalladium(0) (44.89 mg, 0.049 mmol) are added, purged again with argon and stirred at 105° C. for 3 h.

Workup

  1. custompurged again with argon

Sources & evidence

ORD record
ord-d55bed00b7514e41b82e8b63a82244f2
Source dataset
uspto-grants-2015_03
Patent number
US08987249B2

Reaction notes

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