Phosphorus tribromide → 1-(Benzyloxy)-4-bromo-2-(bromomethyl)benzene

HRID 1053991Notes

Reaction equation

HRID 1053991 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:19]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16][Br:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 897136(2-(Benzyloxy)-5-bromophenyl)methanol

Product 1

HCID 117832201-(Benzyloxy)-4-bromo-2-(bromomethyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2-benzyloxy-5-bromo-phenyl)-methanol (4.36 g, 14.87 mmol) in DCM (200 ml) cooled with ice-bath under N2 atmosphere a 1M solution of PBr3 in DCM (14.87 ml, 14.87 mmol) was added. The mixture was stirred at that temperature for 15 min and then at RT overnight. The reaction was quenched with sat. NaHCO3 solution. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to dryness.

Workup

  1. additionwas added
  2. customat RT
  3. customovernight
  4. customThe reaction was quenched with sat. NaHCO3 solution
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-7f51a42635424835a013f752cd99bdba
Source dataset
uspto-grants-2016_07
Patent number
US09394284B2

Reaction notes

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