Phosphorus tribromide → HCID 11074939, compound

HRID 413931Notes

Reaction equation

HRID 413931 reaction equation
[C:1]1([C:7]#[C:8]/[CH:9]=[CH:10]/[CH2:11]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:14]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:14][CH2:11]/[CH:10]=[CH:9]/[C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 546319840317-08-6

Product 1

HCID 11074939HCID 11074939, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-5-phenyl-pent-2-en-4-yn-1-ol (Method 1b) (980 mg, 6.2 mmol) in dry toluene (20 mL) was cooled on ice and phosphorus tribromide (0.59 mL, 6.2 mmol) added slowly. After 16 h at 5° C. the mixture was diluted with ethyl acetate and washed with water (×3). The organic phase was concentrated in vacuo and the residue extracted with heptane (×3). The combined heptane phases were concentrated in vacuo to give 900 mg of crude (E)-(5-bromo-pent-3-en-1-ynyl)-benzene. (According to NMR the product contained ˜5% of the (Z)-isomer).

Workup

  1. additionadded slowly
  2. washwashed with water (×3)
  3. concentrationThe organic phase was concentrated in vacuo
  4. extractionthe residue extracted with heptane (×3)
  5. concentrationThe combined heptane phases were concentrated in vacuo

Sources & evidence

ORD record
ord-e9c520a55db84f41ada36f68a27a7a07
Source dataset
uspto-grants-2003_05
Patent number
US06569901B2

Reaction notes

Loading…