Phosphorus tribromide → 2-Bromomethyl-1,3-dichloro-5-benzyloxy-benzene

HRID 2235236Notes

Reaction equation

HRID 2235236 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([CH2:16]O)=[C:11]([Cl:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:20]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([CH2:16][Br:20])=[C:11]([Cl:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 66621751(4-Benzyloxy-2,6-dichloro-phenyl)methanol

Product 1

HCID 592994282-Bromomethyl-1,3-dichloro-5-benzyloxy-benzeneYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve (4-benzyloxy-2,6-dichloro-phenyl)-methanol in 2.5 L THF and cool to 0° C. under N2. Add 94.45 g PBr3 dropwise and stir at 0° C. for 30 minutes. Pour the reaction mixture into sat'd. NaHCO3 and extract with EtOAc (2×). Dry over Na2SO4, filter and concentrate under vacuum to yield 269 g (89%) of the title compound as a white solid. MS (electrospray), 345.1, 347.1 (ES−).

Workup

  1. additionPour the reaction mixture into sat'd
  2. extractionNaHCO3 and extract with EtOAc (2×)
  3. dry with materialDry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-ec8433d0ea704be6afd9d70fa6573d8d
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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