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

HRID 466228Notes

Reaction equation

HRID 466228 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH2:7]O)=[CH:3][CH:2]=1.P(Br)(Br)[Br:16].C(Cl)Cl.O>CCCCCC.C(OCC)(=O)C>[CH:12]1[CH:13]=[CH:14][C:9]([C:1]2[CH:6]=[CH:5][C:4]([CH2:7][Br:16])=[CH:3][CH:2]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 19186(1,1'-Biphenyl)-4-methanolHCID 24614Phosphorus tribromide

Product 1

HCID 2577161,1'-Biphenyl, 4-(bromomethyl)-

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-biphenylmethanol (62.9 g, 340 mmol) in hexane (650 mL) is treated with phosphorus tribromide (16 mL, 171 mmol) dropwise over 10 minutes. After 20 minutes CH2Cl2 (200 mL) is added to dissolve the remaining solid. The solution is then stirred for 1.5 hours and treated with water (200 mL) and then ethyl acetate. The organic layer is washed with water, cold saturated sodium bicarbonate and water, dried over sodium sulfate and evaporated to dryness to yield 4-biphenylmethyl bromide, m.p. 79°-80° C.

Workup

  1. dissolutionto dissolve the remaining solid
  2. washThe organic layer is washed with water, cold saturated sodium bicarbonate and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b5b875fe91a04f30b1bbf095aa6869d6
Source dataset
uspto-grants-1992_10
Patent number
US05155100

Reaction notes

Loading…