Phosphorus tribromide → 2-Benzyloxy-5-bromomethyl-1,3-dichloro-benzene

HRID 19913Notes

Reaction equation

HRID 19913 reaction equation
P(Br)(Br)[Br:2].[CH2:5]([O:12][C:13]1[C:18]([Cl:19])=[CH:17][C:16]([CH2:20]O)=[CH:15][C:14]=1[Cl:22])[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[C:18]([Cl:19])=[CH:17][C:16]([CH2:20][Br:2])=[CH:15][C:14]=1[Cl:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 16749116(4-Benzyloxy-3,5-dichlorophenyl)methanol

Product 1

HCID 167491172-Benzyloxy-5-bromomethyl-1,3-dichloro-benzene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Phosphorous tribromide (2 mL) was added to a solution of (4-benzyloxy-3,5-dichloro-phenyl)-methanol (CAB02117, 5.50 g, 19.4 mmol) in dichloromethane (80 mL) at 0° C. The mixture was stirred at this temperature for 2 h, diluted with diethyl ether (150 mL), transferred into a separation funnel and washed with water (2×50 mL) and brine (50 mL). The organic layer was dried over magnesium sulphate and concentrated under reduced pressure. The residue was recrystallised from dichloromethane/hexane. 1H-NMR (400 MHz, CDCl3) δ 4.39 (s, 2H, —CH12Br), 5.05 (s, 2H, —CH2Ph), 7.37 (s, 2H), 7.38-7.44 (m, 3H), 7.54-7.58 (m, 2H). 13C-NMR (100 MHz, CDCl3) δ=31.48, 75.39, 128.73, 129.68, 129.70, 129.72, 130.06, 135.46, 136.27, 151.23.

Workup

  1. customtransferred into a separation funnel
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallised from dichloromethane/hexane

Sources & evidence

ORD record
ord-061a6b08f971414da70dc59bc14b4c14
Source dataset
uspto-grants-2010_06
Patent number
US07745472B2

Reaction notes

Loading…