Pyridine → HCID 18950366, compound

HRID 1492378Notes

Reaction equation

HRID 1492378 reaction equation
N1C=CC=CC=1.[C:7]1([CH2:13][C:14]#[C:15][CH2:16]O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.P(Br)(Br)[Br:19]>C1(C)C=CC=CC=1>[Br:19][CH2:16][C:15]#[C:14][CH2:13][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 12474205HCID 12474205, compound

Product 1

HCID 18950366HCID 18950366, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

14.5 ml of pyridine were added to a mixture of 140.4 g (0.96 mol) of 4-phenyl-2-butyn-1-ol (prepared according to G. Dupont, Bull. Soc. Chim. Fr., 1954, page 816) and 600 ml of dry toluene, after which 119.1 g (0.44 mol) of phosphorus tribromide were added dropwise in the course of 2 hours, the temperature not being allowed to exceed 50° C. The mixture was stirred overnight at room temperature and then poured onto 1,000 ml of ice water, the organic phase was separated off and the aqueous phase was extracted several times with methyl tert-butyl ether. The combined organic phases were then washed neutral and dried. The crude product obtained after the solvent had been stripped off under reduced pressure was subjected to fractional distillation. Yield: 126 g of product having a purity of 93% according to gas chromatography; bp.: 83°-85° C. at 0.3 mbar.

Workup

  1. customto exceed 50° C
  2. customthe organic phase was separated off
  3. extractionthe aqueous phase was extracted several times with methyl tert-butyl ether
  4. washThe combined organic phases were then washed neutral
  5. customdried

Sources & evidence

ORD record
ord-2c6fc94e6ba2477bbf53da57998cd8da
Source dataset
uspto-grants-1994_12
Patent number
US05374609

Reaction notes

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