Carbon tetrabromide → 2-(Bromomethyl)-5-methoxybenzonitrile

HRID 1421769Notes

Reaction equation

HRID 1421769 reaction equation
O[CH2:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[C:5]#[N:6].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:33]>C1COCC1>[Br:33][CH2:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 187797672-(Hydroxymethyl)-5-methoxybenzonitrile

Product 1

HCID 126680502-(Bromomethyl)-5-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Hydroxymethyl-5-methoxy-benzonitrile from step 3 (1.12 g, 7.62 mmol) was dissolved in THF (38 ml) and treated with Ph3P (3 g, 11.4 mmol) followed by CBr4 (3.8 g, 11.4 mmol). The reaction mixture was stirred at room temp. for 21 hours. The solvent was removed in vacuo and the residue purified by flash chromatography (15% EtOAc/Hexane) to yield the desired product.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash chromatography (15% EtOAc/Hexane)

Sources & evidence

ORD record
ord-45dfdff55b494650b1f4ea95581471b3
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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