Phosphorus tribromide → HCID 22926823, compound

HRID 1985290Notes

Reaction equation

HRID 1985290 reaction equation
O[CH2:2][C:3]#[C:4][C:5]1[CH:6]=[C:7]([CH2:11][CH:12]([O:18][CH:19]([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:8]=[CH:9][CH:10]=1.P(Br)(Br)[Br:23]>C(COC)OC.C(OCC)(=O)C>[Br:23][CH2:2][C:3]#[C:4][C:5]1[CH:6]=[C:7]([CH2:11][CH:12]([O:18][CH:19]([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 22926886HCID 22926886, compound

Product 1

HCID 22926823HCID 22926823, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

184 mg of Ethyl 3-[3-(3-hydroxy-1-propynyl)phenyl]-2-isopropoxypropanoate was dissolved in 4 ml of dimethoxyethane, and 50 μl of phosphorous tribromide was added. After stirring was continued at room temperature overnight, the reaction mixture was diluted with ethyl acetate and washed with water and 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent was distilled off. Then, the residue was purified by silica gel column chromatography, to give 209 mg of the title compound in the 20:1 hexane-ethyl acetate fraction.

Workup

  1. washwashed with water and 1N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. distillationthe solvent was distilled off
  5. customThen, the residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d0984fafe6bb476d917ceafc35584a4f
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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