Phosphorus tribromide → HCID 20337463, compound

HRID 1706267Notes

Reaction equation

HRID 1706267 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[CH:15]([CH3:19])[CH2:16][CH2:17]O>CCOCC>[Br:2][CH2:17][CH2:16][CH:15]([C:8]1[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=1[O:6][CH3:5])[CH3:19]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 20337490HCID 20337490, compound

Product 1

HCID 20337463HCID 20337463, compound

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-(2,5-dimethoxyphenyl)-1-butanol (30.0 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 compound.

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-bf4c4ae08c524552aa55c60dfac850c6
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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