Phosphorus tribromide → HCID 12903417, compound

HRID 1995702Notes

Reaction equation

HRID 1995702 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:15]([CH3:19])[CH2:16][CH2:17]O)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1>CCOCC>[Br:2][CH2:17][CH2:16][CH:15]([C:9]1[CH:8]=[C:7]([O:6][CH3:5])[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=1)[CH3:19]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 20487368HCID 20487368, compound

Product 1

HCID 12903417HCID 12903417, compoundYield 55%

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-(3,5-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 product; 25 g. (55% yield); b.p. 125°-132° C. at 0.4 mm.

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-09169562099e4ac5a0b1b05247bb676d
Source dataset
uspto-grants-1983_09
Patent number
US04405626

Reaction notes

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