N-bromobutanimide → 2-(Bromomethyl)thiophene-3-carbonitrile

HRID 1251178Notes

Reaction equation

HRID 1251178 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8].[Br:9]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][CH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 125657872-Methylthiophene-3-carbonitrile

Product 1

HCID 225036202-(Bromomethyl)thiophene-3-carbonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

2-Methyl-3-cyanothiophene (2.108 g) was dissolved in benzene (30 ml), followed by the addition of N-bromosuccinimide (4.8 g) and 70% benzoyl peroxide (202 mg), and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was cooled, and the resulting precipitates were filtered off. Then the filtrate was diluted with ethyl acetate, washed with an aqueous solution of saturated sodium bicarbonate, dried (over MgSO4) and then evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow oil (2.746 g, yield; 82%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe resulting precipitates
  3. filtrationwere filtered off
  4. additionThen the filtrate was diluted with ethyl acetate
  5. washwashed with an aqueous solution of saturated sodium bicarbonate
  6. dry with materialdried (over MgSO4)
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-79adb296255f4eb89e315f2b1e037f1a
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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