5-Bromo-3-methyl-1-benzothiophene → 3-Methyl-1-benzothiophene-5-carbonitrile

HRID 487985Notes

Reaction equation

HRID 487985 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:14]=[CH:13][C:8]2[S:9][CH:10]=[C:11]([CH3:12])[C:7]=2[CH:6]=1>CN1CCCC1=O>[C:2]([C:5]1[CH:14]=[CH:13][C:8]2[S:9][CH:10]=[C:11]([CH3:12])[C:7]=2[CH:6]=1)#[N:3]

Participants

4

Reactant 2

HCID 141757645-Bromo-3-methyl-1-benzothiopheneHCID 178418546HCID 178418546, compound

Product 1

HCID 232617323-Methyl-1-benzothiophene-5-carbonitrileYield 90.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To copper (I) cyanide (0.569 g, 6.35 mmol) was added 5-bromo-3-methyl benzo[b]thiophene (1.179 g, 5.19 mmol) in N-methylpyrrolidinone (10 ml) and the mixture was stirred at 180°-190° C. for 17 h. This was then partitioned between ether (75 ml) and ammonia solution (75 ml). The ether layer was separated, washed with more ammonia solution (2×50 ml), dried (Na2SO4) and evaporated in vacuo to leave 0.81 g of an off-white solid. Chromatography on flash silica, eluting with 10% ethyl acetate/petroleum ether yielded 0.76 g (85%) of the title compound as a white solid. δ (CDCl3) 2.47 (3H, s), 7.23 (1H, s), 7.55 (1H, dd, J=8.3 and 1.5 Hz), 7.93 (1H, d, J=8.4 Hz), 8.03 (1H, d, J=1.4 Hz).

Workup

  1. customThis was then partitioned between ether (75 ml) and ammonia solution (75 ml)
  2. customThe ether layer was separated
  3. washwashed with more ammonia solution (2×50 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4bef3d670d5941eaadf54de04d2f6638
Source dataset
uspto-grants-1994_03
Patent number
US05298520

Reaction notes

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