3-Bromo-7-methyl-1-benzothiophene → 3-Cyano-7-methylbenzo[b]thiophene

HRID 649013Notes

Reaction equation

HRID 649013 reaction equation
Br[C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=2[S:5][CH:6]=1.[C:12]([Cu])#[N:13]>N1C=CC=CC=1>[C:12]([C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:4]=2[S:5][CH:6]=1)#[N:13]

Participants

4

Reactant 2

HCID 6150893-Bromo-7-methyl-1-benzothiopheneHCID 178418546HCID 178418546, compound

Product 1

HCID 147804933-Cyano-7-methylbenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3 g of 3-bromo-7-methylbenzo[b]thiophene and 1.1 g CuCN are dissolved in dry pyridine and heated at 220° in an autoclave for 12 hours. The mixture is cooled, concentrated, the residue partitioned between dichloromethane and dilute HCl and the organic phase washed, dried and concentrated. Chromatography of the residue over silica gel (toluene) yields the title compound as pale-yellow crystals. M.p.=82°-84°.

Workup

  1. temperatureheated at 220° in an autoclave for 12 hours
  2. temperatureThe mixture is cooled
  3. concentrationconcentrated
  4. customthe residue partitioned between dichloromethane and dilute HCl
  5. washthe organic phase washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c90280854a7b4e6fafb5bea2ad624009
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

Loading…