Phosphorus tribromide → 5-(Benzyloxy)-2-(bromomethyl)-1,3-dimethylbenzene

HRID 1013807Notes

Reaction equation

HRID 1013807 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16]O)=[C:11]([CH3:18])[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]([CH3:15])[C:12]([CH2:16][Br:20])=[C:11]([CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 67317571(4-(Benzyloxy)-2,6-dimethylphenyl)methanol

Product 1

HCID 114267005-(Benzyloxy)-2-(bromomethyl)-1,3-dimethylbenzeneYield 247.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a solution of (4-Benzyloxy-2,6-dimethyl-phenyl)-methanol (5.70 g, 24 mmol) in THF (100 mL) to 0° C. Treat the solution with Phosphorous tribromide (0.9 mL, 9.4 mmol) and stir the reaction for 2 hr at 0° C. Quench the reaction with water and extract with Et2O. Wash the organic with brine, dry over MgSO4, and filter. Remove the solvent to afford 7.1 g (99%) of product. 1H NMR (d6-CDCl3) δ 7.31-7.43 (m, 5H), 6.65 (s, 2H), 5.01 (s, 2H), 4.56 (s, 2H), 2.38 (s, 6H).

Workup

  1. customthe reaction for 2 hr at 0° C
  2. customQuench
  3. customthe reaction with water
  4. extractionextract with Et2O
  5. washWash the organic with brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customRemove the solvent

Sources & evidence

ORD record
ord-65e8a7db406c4bd993831213a1943845
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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