Carbon tetrabromide → 4-Bromomethyl-2-cyanobiphenyl

HRID 1421774Notes

Reaction equation

HRID 1421774 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.

Workup

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

Sources & evidence

ORD record
ord-20ae4118980b430d95645c5246f85ebc
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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