Carbon tetrabromide → 6,6-Dimethyl-2,4-heptadiynyl bromide

HRID 2248353Notes

Reaction equation

HRID 2248353 reaction equation
O[CH2:2][C:3]#[C:4][C:5]#[C:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:12][CH2:2][C:3]#[C:4][C:5]#[C:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 99893222,4-Heptadiyn-1-ol, 6,6-dimethyl-

Product 1

HCID 193901786,6-Dimethyl-2,4-heptadiynyl bromideYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.0 g (37.3 mmole) of 1-hydroxy-6,6-dimethyl-2,4-heptadiyne and 14.8 g (44.7 mmole) of carbon tetrabromide in 250 mL of H2CCl2 was cooled to 0°-5° C. and 12.7 g (48.4 mmole) of triphenylphosphine was added thereto. The so formed mixture was stirred for 2 hours at 0°-5° C. The reaction mixture was concentrated to about 50 ml and poured into 1 liter of petroleum ether. The mixture was stirred 15 min. and the petroleum ether was removed by decantation. The oily residue was stirred for 15 min. with another 1 liter of petroleum ether which was decanted off. The combined petroleum ether extracts were concentrated to an oil which was chromatographed on silica gel, eluting with petroleum ether to give 6.87 g of the title compound, M/e, M+ 200.

Workup

  1. customThe so formed mixture
  2. concentrationThe reaction mixture was concentrated to about 50 ml
  3. additionpoured into 1 liter of petroleum ether
  4. stirringThe mixture was stirred 15 min.
  5. customthe petroleum ether was removed by decantation
  6. stirringThe oily residue was stirred for 15 min. with another 1 liter of petroleum ether which
  7. customwas decanted off
  8. concentrationThe combined petroleum ether extracts were concentrated to an oil which
  9. customwas chromatographed on silica gel
  10. washeluting with petroleum ether

Sources & evidence

ORD record
ord-9044218bae784fb6be6c6a18e7ce752b
Source dataset
uspto-grants-1991_08
Patent number
US05039676

Reaction notes

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