Carbon tetrabromide → 4-(Bromomethyl)benzene-1,2-dicarbonitrile

HRID 1585936Notes

Reaction equation

HRID 1585936 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:11]#[N:12])[C:6](=[CH:9][CH:10]=1)[C:7]#[N:8].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:4]=[C:5]([C:11]#[N:12])[C:6](=[CH:9][CH:10]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18779681HCID 18779681, compound

Product 1

HCID 187797764-(Bromomethyl)benzene-1,2-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxymethyl-phthalonitrile from step 2 (1.3 g, 8.2 mmol) was dissolved in THF (41 ml) and treated with Ph3P (3.2 g, 12.3 mmol) followed by CBr4 (4 g, 12.3 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. FAB MS: 222 m/z (M+ +H)

Workup

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

Sources & evidence

ORD record
ord-54025b39475040fbb0c53cd9b00fe561
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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