Carbon tetrabromide → 4-(Bromomethyl)-2-methoxybenzonitrile

HRID 1585940Notes

Reaction equation

HRID 1585940 reaction equation
O[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH3:12])[CH:4]=1.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:6]([C:7]#[N:8])=[C:5]([O:11][CH3:12])[CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22016838HCID 22016838, compound

Product 1

HCID 219850074-(Bromomethyl)-2-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-hydroxymethyl-2-methoxy-benzonitrile (from L-819,538, step 2, 2.0 g, 12.3 mmol) was dissolved in THF (61.5 ml) and treated with Ph3P (4.82 g, 18.4 mmol) followed by CBr4 (6.1 g, 18.4 mmol). The reaction was mixture stirred at room temp. for 17 hours. The solvent was removed in vacuo and the residue was purified by flash chromatography (10% EtOAc/Hexane) to yield the desired product. FAB MS: 226w m/z (M+ +H)

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography (10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-bcf69122456e449ba484b77da20b9e33
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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