Carbon tetrabromide → 4-Bromomethyl-2-cyanobiphenyl

HRID 1585947Notes

Reaction equation

HRID 1585947 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:15]#[N:16])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:37]>C1COCC1>[Br:37][CH2:2][C:3]1[CH:4]=[C:5]([C:15]#[N:16])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 187797454-Hydroxymethylbiphenyl-2-carbonitrile

Product 1

HCID 222385014-Bromomethyl-2-cyanobiphenyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Hydroxymethyl-biphenyl-2-carbonitrile from step 3 (1.3 g, 6.2 mmol) was dissolved in THF (31 ml) and treated with Ph3P (2.4 g, 9.3 mmol) followed by CBr4 (3 g, 9.3 mmol). The reaction was mixture stirred at room temp. for 16 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: m/z 272 (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-1fb74cd68e7d46538d18a3ea2318b6cb
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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