Phosphorus tribromide → 1-Benzyloxy-4-bromomethyl-2-chloro-benzene

HRID 19918Notes

Reaction equation

HRID 19918 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][C:14]=1[Cl:21])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl.C(OCC)C>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][Br:2])=[CH:15][C:14]=1[Cl:21])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 21976852(4-Benzyloxy-3-chloro-phenyl)-methanol

Product 1

HCID 109689681-Benzyloxy-4-bromomethyl-2-chloro-benzene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Phosphorous tribromide (2 mL) was added to a solution of (4-benzyloxy-3-chlorophenyl)-methanol (CAB02127, 3.40 g, 13.7 mmol) in dichloromethane (50 mL) at 0° C. The mixture was stirred at this temperature for 1 h, diluted with diethyl ether (100 mL), transferred into a separation funnel and washed with water (50 mL) and brine (50 mL). The organic layer was dried over magnesium sulphate and concentrated under reduced pressure to give a white, analytical pure solid. Yield: 4.27 g (100%).

Workup

  1. customtransferred into a separation funnel
  2. washwashed with water (50 mL) and brine (50 mL)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto give a white, analytical pure solid

Sources & evidence

ORD record
ord-56d1c683e4564eb18c557ac0451208c7
Source dataset
uspto-grants-2010_06
Patent number
US07745472B2

Reaction notes

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