Phosphorus tribromide → 4-(Bromomethyl)-3-methylphenyl phenylmethyl ether

HRID 1946387Notes

Reaction equation

HRID 1946387 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:16]O.P(Br)(Br)[Br:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:10]1([CH2:9][O:8][C:6]2[CH:5]=[CH:4][C:3]([CH2:16][Br:19])=[C:2]([CH3:1])[CH:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 23077848(4-(Benzyloxy)-2-methylphenyl)methanol

Product 1

HCID 667708914-(Bromomethyl)-3-methylphenyl phenylmethyl etherYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of {2-methyl-4-[(phenylmethyl)oxy]phenyl}methanol (1.49 g, 6.53 mmol) in DCM (20 ml) under nitrogen in an ice-water bath was added a solution of phosphorus tribromide (0.62 ml, 6.57 mmol, Aldrich) in DCM (10 ml). The solution was allowed to warm to ambient temperature and stirred for 3 h. The reaction mixture was poured onto ice-water (70 ml) and saturated aqueous sodium hydrogen carbonate (30 ml). The mixture was diluted with DCM (50 ml) and the phases separated. The aqueous extract was washed with dichloromethane DCM (20 ml). The combined organic extracts were washed with water (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to leave 4-(bromomethyl)-3-methylphenyl phenylmethyl ether as a yellow oil (1.72 g).

Workup

  1. customthe phases separated
  2. extractionThe aqueous extract
  3. washwas washed with dichloromethane DCM (20 ml)
  4. washThe combined organic extracts were washed with water (50 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d4f2f6c71efa472bab81c910bf14bbb2
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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