Nitrogen → 3-(Methylthio)-2-phenylthiophene

HRID 1990062Notes

Reaction equation

HRID 1990062 reaction equation
I[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[S:7][CH3:8].Br[C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].N#N>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(O)C.C(COC)OC>[CH3:8][S:7][C:6]1[CH:5]=[CH:4][S:3][C:2]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 579753072-Iodo-3-(methylsulfanyl)thiophene

Product 1

HCID 685221633-(Methylthio)-2-phenylthiopheneYield 82.7%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Degas a solution of 2-iodo-3-methylsulfanyl-thiophene (18 g, 70.3 mmol), 4-bromobenzeneboronic acid (14.1 g, 70.3 mmol), potassium carbonate (21.4 g, 155 mmol), tetrakis(triphenylphosphine)-palladium (0) (8.1 g, 7.02 mmol) in a mixture of anhydrous dimethoxyethane (300 ml) and absolute ethanol (150 ml) with Ar or N2 for 15 min and stir for 12 hours at 80° C. Cool the reaction mixture to room temperature, add water (100 ml) and extract the crude product with dichloromethane (3×150 ml). Purify the title compound by column chromatography using hexane as eluent solvent yielding the title compound 12 g (60%) as a white solid.

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. extractionextract the crude product with dichloromethane (3×150 ml)
  3. customPurify the title compound by column chromatography

Sources & evidence

ORD record
ord-d956f019ff9b4a17966bd351c73d1b23
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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