2-Acetylthiophene → 2-Phenyl-1-(2-thienyl)ethanone

HRID 2267438Notes

Reaction equation

HRID 2267438 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](=[O:15])[CH3:14].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:2]1([CH2:14][C:13]([C:9]2[S:8][CH:12]=[CH:11][CH:10]=2)=[O:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 69202-AcetylthiopheneHCID 7961BromobenzeneHCID 634876Binap, (A+-)-HCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 6870902-Phenyl-1-(2-thienyl)ethanoneYield 41.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

1-Bromobenzene (2 g, 12 mmol) in toluene (30 mL) was treated 1-(thiophen-2-yl)ethanone (1.8 g, 14.4 mmol), potassium bis(trimethylsilyl)amide (28.8 mL of 0.5 M solution in toluene, 14.4 mmol), 2,2′-bis(diphenyl)phosphino-1,1′-binaphthyl (racemic BINAP, 1.86 g, 3 mmol). The reaction was heated to 90° C. in an oil bath under a nitrogen atmosphere. After 4 h, the reaction was allowed to cool to room temperature and diluted with ethyl acetate (30 mL). The organic layer was washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried with sodium sulfate, concentrated and purified by flash chromatography using a gradient of 10 to 40% ethyl acetate in hexanes to yield a yellow oil (1 g). MS (M+H)+ 203.

Workup

  1. temperatureto cool to room temperature
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water and brine
  3. dry with materialThe organic layer was then dried with sodium sulfate
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9541db40e7bd42a4ac3f09e609f08fc4
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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