Carbon tetrabromide → 1-Bromopentadec-2-yne

HRID 617851Notes

Reaction equation

HRID 617851 reaction equation
C(OCC[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1)(=O)C.[C:21](Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:21]([Br:22])[C:9]#[C:8][CH2:7][CH2:12][CH2:11][CH2:10][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 114827792-(4-octylphenyl)ethyl Acetate

Product 1

HCID 150032421-Bromopentadec-2-yne

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a reaction vessel equipped with a calcium chloride tube, 8.465 g of the compound of (2) above was dissolved in 85 ml of dichloromethane and 15.683 g of carbon tetrabromide and 14.867 g of triphenylphosphine were added thereto under ice-cooling. The mixture was stirred at 0° C. for 5 minutes. The reaction mixture was concentrated under reduced pressure and the residue was extracted with hexane. The hexane extract obtained was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give 7.964 g of 2-pentadecynyl bromide.

Workup

  1. customIn a reaction vessel equipped with a calcium chloride tube
  2. temperatureunder ice-cooling
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionthe residue was extracted with hexane
  5. extractionThe hexane extract
  6. customobtained
  7. concentrationwas concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-828e57946f5742b6956f3d6c81022b09
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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