Phosphorus tribromide → 4-Bromo-2-(3,5-dimethoxyphenoxy)benzyl Bromide

HRID 394621Notes

Reaction equation

HRID 394621 reaction equation
P(Br)(Br)[Br:2].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10]O)=[C:8]([O:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=2)[CH:7]=1>C(Cl)Cl>[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][Br:2])=[C:8]([O:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 20631745HCID 20631745, compound

Product 1

HCID 234318434-Bromo-2-(3,5-dimethoxyphenoxy)benzyl BromideYield 224.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an argon atmosphere, 4.7 mL (F.W. 270.70, d=2.850, 49.5 mmol) of phosphorus tribromide was added to a solution of 46 g (F.W. 339.19, 135 mmol) of alcohol (23) in 100 mL of methylene chloride at 0° C. and stirred at room temperature for 30 minutes. To the reaction mixture was added ice water and the resulting solution was further stirred at room temperature for 30 minutes. The obtained solution was extracted with ethyl acetate and the extract was washed with water and then with a saturated sodium chloride aqueous solution. The resulting extract was dried with anhydrous magnesium sulfate and then, concentrated. The residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:5) to obtain 44.6 g (84%) of a bromide (24). (TLC; ethyl acetate:hexane=1:4)

Workup

  1. stirringthe resulting solution was further stirred at room temperature for 30 minutes
  2. extractionThe obtained solution was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. extractionThe resulting extract
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-a1f2ac47b3dc44b487e24ca1163b2f6d
Source dataset
uspto-grants-2003_08
Patent number
US06602898B1

Reaction notes

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