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

HRID 1421740Notes

Reaction equation

HRID 1421740 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-1d2e9baa34d04a388f788deba128efaf
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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