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

HRID 1585942Notes

Reaction equation

HRID 1585942 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-4a3c3407a03748b38aff669869dbd128
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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