Phosphorus tribromide → Benzene, 1-(bromomethyl)-3-methoxy-2-(phenylmethoxy)-

HRID 982112Notes

Reaction equation

HRID 982112 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH2:15]O)=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:20]>C(OCC)C>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][Br:20])=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 927250(2-(Benzyloxy)-3-methoxyphenyl)methanol

Product 1

HCID 10852231Benzene, 1-(bromomethyl)-3-methoxy-2-(phenylmethoxy)-Yield 131.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 15.04 g (62 mmol) of 2-benzyloxy-3-hydroxymethyl-1-methoxybenzene, from Step 2, in 140 mL of diethyl ether at 0° C. was added slowly, with stirring, 2.9 mL (31 mmol) of phosphorous tribromide. The reaction mixture was stirred at 0° C. for 30 minutes and then allowed to warm to ambient temperature over a 4 h period. The solution phase was decanted and the reaction was quenched with aqueous sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted twice with diethyl ether. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 12.48 g (65% yield) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  2. customThe solution phase was decanted
  3. customthe reaction was quenched with aqueous sodium bicarbonate solution
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted twice with diethyl ether
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10e4ed91b7df455f810d8a3a426ad410
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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