2-Acetyl-3-bromothiophene → HCID 45085804, compound

HRID 911430Notes

Reaction equation

HRID 911430 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1Br)(=[O:3])[CH3:2].[Cu](C#N)[C:11]#[N:12]>CN1C(=O)CCC1.O>[C:1]([C:4]1[S:5][CH:6]=[CH:7][C:8]=1[C:11]#[N:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 27644962-Acetyl-3-bromothiopheneHCID 178418260HCID 178418260, compound

Product 1

HCID 45085804HCID 45085804, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a stirred solution of 2-acetyl-3-bromothiophene (1.49 g, 7.29 mmol) (Chem. Pharm. Bull. 2000, 48, 1558-1566) in dry NMP (72 mL) for 10 h at 150° C. in the presence of copper cyanide (3.26 g, 36.5 mmol). Dilute the mixture with water, extract three times with diethyl ether, dry over anhydrous Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (10:1) to give the desired intermediate as a dark oil (1.1 g, 99%).

Workup

  1. extractionextract three times with diethyl ether
  2. dry with materialdry over anhydrous Na2SO4
  3. concentrationconcentrate in vacuo
  4. customPurify by chromatography on silica gel eluting with hexane/EtOAc (10:1)

Sources & evidence

ORD record
ord-518b5962e0174d18bdeb606d5353465b
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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