Dimethyl Sulfide → HCID 18380364, compound

HRID 382180Notes

Reaction equation

HRID 382180 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([N:7]2[CH:11]=[CH:10][CH:9]=[CH:8]2)=[CH:3][CH:2]=1.CSC.C(#N)C.[Br:24]Br>C(Cl)Cl>[C:1]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][C:4]([N:7]2[CH:11]=[CH:10][C:9]([Br:24])=[CH:8]2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6342AcetonitrileHCID 24408BromineHCID 4763727HCID 4763727, compound

Product 1

HCID 18380364HCID 18380364, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

To a mixture of N-biphenyl-4-yl-1H-pyrrole (500 mg, 2.28 mmol), dimethylsulfide (0.25 mL, 3.4 mmol), CH2Cl2 (30 mL), and acetonitrile (10 mL) at −10° C. was added dropwise a solution of bromine in CH2Cl2 (5 mL) over 15 minutes. The mixture was allowed to warm to 10° C. over 2 hours. The resultant mixture was washed with 1M pH 7 phosphate buffer (50 mL) and extracted with CH2Cl2 (25 mL). The combined organic layers were dried over Na2SO4 and concentrated to a crude residue which was purified via flash column chromatography with 0-10% CH2Cl2/hex gradient eluant to furnish 240 mg (40%) of N-(biphenyl-4-yl)-3-bromo-1H-pyrrole as a white solid, mp 141-3° C.

Workup

  1. washThe resultant mixture was washed with 1M pH 7 phosphate buffer (50 mL)
  2. extractionextracted with CH2Cl2 (25 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to a crude residue which
  5. customwas purified via flash column chromatography with 0-10% CH2Cl2/hex gradient eluant

Sources & evidence

ORD record
ord-dd1c4e05849f4cc3a4769b52175aa3d5
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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