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

HRID 2041313Notes

Reaction equation

HRID 2041313 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-7a929f2ddaab4ee78219a7cb2a155a69
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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