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

HRID 536571Notes

Reaction equation

HRID 536571 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-50f70637c3354f6f898c326181e72d06
Source dataset
uspto-grants-2014_10
Patent number
US08859606B2

Reaction notes

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