Phosphorus tribromide → HCID 12903417, compound

HRID 435133Notes

Reaction equation

HRID 435133 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 phosphorus 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-4467da202b264123af7790c0816b3f8a
Source dataset
uspto-grants-1983_08
Patent number
US04400385

Reaction notes

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