Carbon tetrabromide → 5-(Bromomethyl)thiophene-3-carbonitrile

HRID 2297942Notes

Reaction equation

HRID 2297942 reaction equation
O[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>ClCCl>[Br:30][CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 107254165-(Hydroxymethyl)thiophene-3-carbonitrile

Product 1

HCID 108457645-(Bromomethyl)thiophene-3-carbonitrileYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 2-(hydroxymethyl)thiophene-4-carbonitrile (1.14 g, 8.2 mmol) in dichloromethane (50 mL) was added triphenylphosphine (2.8 g, 10.6 mmol) and carbon tetrabromide (3.3 g, 9.9 mmol). After stirring for 3 h at rt, the solvent was removed in vacuo and the residue chromatographed using EtOAc and n-hexane (1:4) to give the title compound (1.6 g, 96%).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue chromatographed

Sources & evidence

ORD record
ord-64d1390e144b4c2ca2aa9d9ea069fe61
Source dataset
uspto-grants-2002_12
Patent number
US06492402B1

Reaction notes

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