Benzoyl Peroxide → 2-(Bromomethyl)thiophene-3-carbonitrile

HRID 1710831Notes

Reaction equation

HRID 1710831 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.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1.CCOC(C)=O>[Br:9][CH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 125657872-Methylthiophene-3-carbonitrile

Product 1

HCID 225036202-(Bromomethyl)thiophene-3-carbonitrileYield 46.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-thiophene-3-carbonitrile [see Beaton, et al.; Tetrahedron Lett. 39, 10, 1998, 1227-1230] (1.36 g, 11 mmol), N-bromosuccinimide (2.56 g, 14.4 mmol), and a catalytic amount of benzoyl peroxide were stirred in benzene (30 mL) at 80° C. for 2h. The solution was diluted with EtOAc, washed with sat. NaHCO3 and brine, dried (MgSO4), and concentrated in vacuo. Purification by silica gel chromatography (10% EtOAc/hexanes) gave 1.03 g (46%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): 7.39 (d, 1H, J=5.6 Hz), 7.17 (d, 1H, J=5.6 Hz), 4.79 (s, 2H).

Workup

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by silica gel chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9d53aac0bc4a473791a22adfbf1aa720
Source dataset
uspto-grants-2010_09
Patent number
US07790736B2

Reaction notes

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