Carbon Tetrachloride → 1,1-Dibromo-2-(4-ethylphenyl)ethylene

HRID 1577031Notes

Reaction equation

HRID 1577031 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.[CH2:30]([C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1)[CH3:31]>[Zn].C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:36][C:35]1[CH:38]=[CH:39][C:32]([CH2:30][CH3:31])=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 208614-Ethylbenzaldehyde

Product 1

HCID 214353101,1-Dibromo-2-(4-ethylphenyl)ethylene

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4.94 g. (0.015 mol.) of carbon tetrabromide, 3.90 g. (0.015 mol.) of triphenylphosphine and 0.975 g. (0.015 g.-atom) of zinc in 25 ml. of carbon tetrachloride is stirred at 25° for 24 hours. A solution of 1.0 g. (7.45 mmol.) of p-ethylbenzaldehyde in 10 ml. of methylene chloride is added and the reaction mixture is stirred an additional two hours. Petroleum ether (140 ml.) is added to the mixture, the organic layer is decanted and the residue is extracted with 1:4 methylene chloride-petroleum ether. The combined organic solutions are concentrated under reduced pressure to give 1,1-dibromo-2-(4-ethylphenyl)ethylene.

Workup

  1. additionA mixture of 4.94 g
  2. customthe organic layer is decanted
  3. extractionthe residue is extracted with 1:4 methylene chloride-petroleum ether
  4. concentrationThe combined organic solutions are concentrated under reduced pressure

Sources & evidence

ORD record
ord-2ac84c6a5e884dd1bbf33b66ca94bce4
Source dataset
uspto-grants-1976_09
Patent number
US03983245

Reaction notes

Loading…