Carbon tetrabromide → 3-(Bromomethyl)thiophene-2-carbonitrile

HRID 1952841Notes

Reaction equation

HRID 1952841 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH2:8]O)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:29]C(Br)(Br)Br>C1COCC1>[Br:29][CH2:8][C:7]1[CH:6]=[CH:5][S:4][C:3]=1[C:1]#[N:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 218664902-Cyano-3-hydroxymethylthiophene

Product 1

HCID 135530813-(Bromomethyl)thiophene-2-carbonitrileYield 110.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11.7 g (84.07 mmol) of 2-cyano-3-hydroxymethylthiophene were dissolved together with 24.1 g (91.87 mmol) of triphenylphosphine in 100 ml of THF at room temperature and, while cooling (ice bath), 30.47 g (91.87 mmol) of tetrabromomethane were added in portions. Stirring at room temperature for 3 hours was followed by concentration under reduced pressure and purification by chromatography on silica gel (methylene chloride/petroleum ether) to result in 18.8 g of pale yellow crystalline product still containing petroleum ether.

Workup

  1. additionwere added in portions
  2. concentrationwas followed by concentration under reduced pressure and purification by chromatography on silica gel (methylene chloride/petroleum ether)

Sources & evidence

ORD record
ord-b32d28022c9e48baae1e8c8dfc583868
Source dataset
uspto-grants-2000_09
Patent number
US06114358

Reaction notes

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