Carbon tetrabromide → 3-Benzyloxy-4-bromomethylbenzonitrile

HRID 2184238Notes

Reaction equation

HRID 2184238 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[CH2:17]O)[C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[CH2:17][Br:20])[C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 224760973-Benzyloxy-4-hydroxymethylbenzonitrile

Product 1

HCID 224760993-Benzyloxy-4-bromomethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.3 g (18 mmol) of the alcohol (a) underwent substitution in 40 ml of THF with 7.9 g (24 mmol) of CBr4 and 6.3 g (24 mmol) of PPh3, which was added in portions over the course of 30 min. The reaction mixture was stirred at RT for 20 h. The product was purified by column chromatography (mobile phase: t-butyl methyl ether/petroleum ether 2:1). 4.6 g were obtained.

Workup

  1. customThe product was purified by column chromatography (mobile phase: t-butyl methyl ether/petroleum ether 2:1)
  2. custom4.6 g were obtained

Sources & evidence

ORD record
ord-2c0be20f28d84e488a3ed5e540001a71
Source dataset
uspto-grants-2005_05
Patent number
US06900319B2

Reaction notes

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