4'-Bromoacetanilide → N-(4-thiophen-3-yl-phenyl)-acetamide

HRID 1665695Notes

Reaction equation

HRID 1665695 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[S:7]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8]1.Br[C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[S:7]1[CH:11]=[CH:10][C:9]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=2)=[CH:8]1

Participants

8

Reactant 4

HCID 76834'-BromoacetanilideHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 581760Thiophene-3-boronic acid

Product 1

HCID 57875827N-(4-thiophen-3-yl-phenyl)-acetamideYield 63.44%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of toluene (7.5 mL) and water (3 mL) was degassed with argon for 10 min, to which sodium carbonate (297 mg, 2.8 mmol) was added and the mixture was further degassed with argon for 5 min. Thiophene-3-boronic acid (215 mg, 1.68 mmol) and N-(4-bromo-phenyl)-acetamide (300 mg, 2.27 mmol) were added and the mixture was degassed with argon for another 10 min. To the above resulting mixture was added tetrakispalladium triphenylphosphine (161 mg, 0.14 mmol) and the mixture was degassed with argon for another 10 min. The resulting reaction mixture was heated to reflux for 3 hrs. After completion, the reaction mixture was diluted with ethyl acetate and washed with water followed by brine solution. The ethyl acetate layer collected was dried over sodium sulphate and concentrated under reduced pressure. Purification by column chromatography, (using silica gel 60-120 and 35% ethyl acetate in hexane as eluent) afforded 193 mg (63.44% Yield) of N-(4-thiophen-3-yl-phenyl)-acetamide.

Workup

  1. additionwas added
  2. customthe mixture was further degassed with argon for 5 min
  3. customthe mixture was degassed with argon for another 10 min
  4. customthe mixture was degassed with argon for another 10 min
  5. customThe resulting reaction mixture
  6. temperaturewas heated
  7. temperatureto reflux for 3 hrs
  8. washwashed with water
  9. customThe ethyl acetate layer collected
  10. dry with materialwas dried over sodium sulphate
  11. concentrationconcentrated under reduced pressure
  12. customPurification by column chromatography, (using silica gel 60-120 and 35% ethyl acetate in hexane as eluent)

Sources & evidence

ORD record
ord-ecf0e14952f94209a025052e07500d0f
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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