Carbon tetrabromide → HCID 20331219, compound

HRID 2057639Notes

Reaction equation

HRID 2057639 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([CH2:12][CH2:13][CH:14]=O)=[CH:10][CH:9]=1>[Zn].C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:14][CH2:13][CH2:12][C:11]1[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 11205Carbon tetrabromideHCID 111266073-(4-Methoxyphenyl)propanal

Product 1

HCID 20331219HCID 20331219, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 39.2 g. of zinc dust, 157 g. of triphenylphosphene and 200 g. of carbon tetrabromide in 500 ml. methylene chloride is stirred at room temperature for 25 hours. To the resultant solution is added 50 g. of 4-methoxyhydrocinnamaldehyde and stirring is continued for an additional 2 hours. The solution is diluted with 2 l. of pentane and the precipitate is filtered. The precipitate is stirred with 100 ml. methylene chloride, diluted with 400 ml. pentane, and again filtered. The organic solutions are combined and evaporated to yield 1,1-dibromo-4-(4-methoxyphenyl)-1-butene as a light yellow oil.

Workup

  1. additionThe solution is diluted with 2 l
  2. filtrationof pentane and the precipitate is filtered
  3. additionmethylene chloride, diluted with 400 ml
  4. filtrationpentane, and again filtered
  5. customevaporated

Sources & evidence

ORD record
ord-0acf5f9d03694289bfb7c4c2b5fb0b75
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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