(1,1'-Biphenyl)-4-methanol → 1,1'-Biphenyl, 4-(bromomethyl)-

HRID 2228669Notes

Reaction equation

HRID 2228669 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH2:11]O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:16]>C(OC(C)C)(C)C.C(Cl)(Cl)Cl.O>[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][Br:16])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 19186(1,1'-Biphenyl)-4-methanolHCID 24614Phosphorus tribromide

Product 1

HCID 2577161,1'-Biphenyl, 4-(bromomethyl)-Yield 111.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of 4-phenylbenzyl alcohol (1.00 g, 5.43 mmol) in a mixture of diisopropyl ether (10 mL) and chloroform (20 mL) was added phosphorus tribromide (0.98 g, 3.62 mmol) with ice-cooling and the mixture was stirred at room temperature for 1 hour. This reaction mixture was diluted with water and extracted with diisopropyl ether. The organic layer was washed with water and saturated aqueous sodium hydrogen carbonate solution, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was recrystallized from ethanol-hexane to provide 1.00 g of the title compound. Yield 75%.

Workup

  1. temperaturecooling
  2. extractionextracted with diisopropyl ether
  3. washThe organic layer was washed with water and saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-344cd6733bb24b3e901ddf9ea307ebce
Source dataset
uspto-grants-2002_07
Patent number
US06417213B2

Reaction notes

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