Carbon tetrabromide → 4-Bromomethyl-2-(2,2,2-trifluoro-ethoxy)-benzonitrile

HRID 1585917Notes

Reaction equation

HRID 1585917 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[CH:12]=[C:11]([CH2:13]O)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:37]>C1COCC1>[Br:37][CH2:13][C:11]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:4][CH2:3][C:2]([F:16])([F:15])[F:1])[CH:12]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 187796882-(2,2,2-Trifluoro-ethoxy)-4-hydroxymethyl-benzonitrile

Product 1

HCID 187797974-Bromomethyl-2-(2,2,2-trifluoro-ethoxy)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2,2,2-Trifluoro-ethoxy)-4-hydroxymethyl-benzonitrile (1.4 g, 6.1 mmol) was dissolved in THF (31 ml) and treated with Ph3P (2.4 g, 9.15 mmol) followed by CBr4 (3 g, 9.15 mmol). The reaction mixture was stirred at room temp. for 2 hours. The solvent was removed in vacuo and the residue purified by flash chromatography (20% EtOAc/Hexane) to yield the desired product.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash chromatography (20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-8797ec7764d84703a8edb7b1d9f21b70
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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