Carbon tetrabromide → 1,1-Dibromo-3-cyclohexyl-1-propene

HRID 2379021Notes

Reaction equation

HRID 2379021 reaction equation
[Br:1][C:2]([Br:5])(Br)Br.[CH:6]1([CH2:12][CH:13]=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]([Br:5])=[CH:13][CH2:12][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 3166272-Cyclohexylacetaldehyde

Product 1

HCID 110658841,1-Dibromo-3-cyclohexyl-1-propeneYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 76.36 g of tetrabromomethane in 100 ml of CH2Cl2 is added dropwise at -10° C. to a solution of 0.2 mol of cyclohexylacetaldehyde and 104.8 g of triphenylphosphine in 150 ml of CH2Cl2. After stirring at room temperature for 30 min, the mixture is filtered with suction, concentrated and purified on silica gel using petroleum ether as the eluent. 48 g of the title compound are obtained as an oil.

Workup

  1. filtrationthe mixture is filtered with suction
  2. concentrationconcentrated
  3. custompurified on silica gel

Sources & evidence

ORD record
ord-257a36ecd6714d56b58c6f38f49d4688
Source dataset
uspto-grants-1994_11
Patent number
US05360791

Reaction notes

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