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

HRID 901149Notes

Reaction equation

HRID 901149 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-chloro-phenyl)-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-c13ab4f8f87f46ce9fb2bd954e1ab451
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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