Phosphorus tribromide → 1-Bromo-3-(3-methoxyphenyl)butane

HRID 1111766Notes

Reaction equation

HRID 1111766 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]([CH3:17])[CH2:14][CH2:15]O)[CH:10]=[CH:11][CH:12]=1>CCOCC>[Br:2][CH2:15][CH2:14][CH:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][CH3:5])[CH:8]=1)[CH3:17]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 139885203-(3-Methoxyphenyl)-1-butanol

Product 1

HCID 204969191-Bromo-3-(3-methoxyphenyl)butane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of phosphorous tribromide (5.7 ml., 0.06 mole) in ether (30 ml.) is added to a solution of 3-(3-methoxyphenyl)-1-butanol (25.8 g., 0.143 mole) in ether (20 ml.) at -5° C. to -10° C. and the reaction mixture stirred at -5° C. to -10° C. for 2.5 hours. It is then warmed to room temperature and stirred for an additional 30 minutes. The mixture is poured over ice (200 g.) and the resulting mixture extracted with ether (3 × 50 ml.). The combined extracts are washed with 5% sodium hydroxide solution (3 × 50 ml.), saturated sodium chloride solution (1 × 50 ml.) and dried (Na2SO4). Removal of the ether and vacuum distillation of the residue affords the title product.

Workup

  1. stirringstirred for an additional 30 minutes
  2. extractionthe resulting mixture extracted with ether (3 × 50 ml.)
  3. washThe combined extracts are washed with 5% sodium hydroxide solution (3 × 50 ml.), saturated sodium chloride solution (1 × 50 ml.)
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the ether and vacuum distillation of the residue

Sources & evidence

ORD record
ord-a011bbf06b1b405f81cd65fed626aebb
Source dataset
uspto-grants-1978_10
Patent number
US04118559

Reaction notes

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