Phosphorus tribromide → HCID 19981886, compound

HRID 1460457Notes

Reaction equation

HRID 1460457 reaction equation
O[CH:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].P(Br)(Br)[Br:19]>C1C=CC=CC=1>[Br:19][CH:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 122605Benzeneacetic acid, .alpha.-hydroxy-3,4-dimethoxy-, ethyl ester

Product 1

HCID 19981886HCID 19981886, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-hydroxy-2-(3,4-dimethoxyphenyl)acetate (19.5 g) in benzene (200 ml) was added phosphorus tribromide (8.18) dropwise at 50° C. and the mixture was stirred at 60° C. for one hour. The reaction mixture was then washed successively with water, saturated aqueous solution of NaHCO3 and water and dried (MgSO4). The benzene was distilled off and the residue was subjected to silica gel chromatography. From the fraction eluted by ethyl acetate-hexane (1:3, v/v), ethyl 2-bromo-2-(3,4-dimethoxyphenyl)acetate (18.5 g, yield 75%) was obtained as an oil.

Workup

  1. washThe reaction mixture was then washed successively with water, saturated aqueous solution of NaHCO3 and water
  2. dry with materialdried (MgSO4)
  3. distillationThe benzene was distilled off
  4. washFrom the fraction eluted by ethyl acetate-hexane (1:3

Sources & evidence

ORD record
ord-cd0d5babd3c54a6fb5fdc3ea610d0e88
Source dataset
uspto-grants-1991_12
Patent number
US05071841

Reaction notes

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