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

HRID 268393Notes

Reaction equation

HRID 268393 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 2 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-7bb20d0c84d5402d85f03096af2ddde4
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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