Phosphorus tribromide → 3-(Bromomethyl)biphenyl

HRID 2296964Notes

Reaction equation

HRID 2296964 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:16]>CCCCCC>[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][Br:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 6035563-Biphenylmethanol

Product 1

HCID 38644053-(Bromomethyl)biphenylYield 198.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of 5.57 g (30 mmol) of 3-phenylbenzylalcohol in n-hexane was added dropwise 4.06 g (13.5 mmol) of phosphorous tribromide with ice-cooling. The mixture was removed from an ice bath and stirred at room temperature for 3.5 hours. To the reaction mixture were added ice water and tert-butyl methyl ether and the mixture was stirred for 30 minutes and separated. The organic layer was washed twice with water, dried and concentrated to obtain 6.62 g (26.8 mmol) of 3-phenylbenzylbromide.

Workup

  1. temperaturecooling
  2. customThe mixture was removed from an ice bath
  3. additionTo the reaction mixture were added ice water and tert-butyl methyl ether
  4. stirringthe mixture was stirred for 30 minutes
  5. customseparated
  6. washThe organic layer was washed twice with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6de059ecaacd42499539fe8e53f59730
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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