Carbon tetrabromide → HCID 15431059, compound

HRID 1977705Notes

Reaction equation

HRID 1977705 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:36])([CH3:35])[CH:33]=O)=[CH:28][CH:27]=1>C(Cl)Cl.[Zn]>[Br:21][C:20]([Br:24])=[CH:36][C:32]([C:29]1[CH:28]=[CH:27][C:26]([Cl:25])=[CH:31][CH:30]=1)([CH3:33])[CH3:35]

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 114353342-(4-Chlorophenyl)-2-methylpropanal

Product 1

HCID 15431059HCID 15431059, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A solution of triphenyl phosphine (89.34 g, 0.34 mol) in methylene chloride is added dropwise to a mixture of zinc powder (22.27 g, 0.34 mol) and carbon tetrabromide (112.8 g, 0.34 mol) in methylene chloride at 20° C. over one hour. The resultant mixture is stirred at room temperature overnight, treated dropwise with a solution of 2-(p-chlorophenyl)-2-methylpropionaldehyde (31.1 g, 0.17 mol) in methylene chloride over 20 minutes, refluxed for 2 days, and poured into petroleum ether. The organic mixture is filtered through diatomaceous earth and concentrated in vacuo to obtain a residue. The residue is distilled to give the title product as an oil (38.5 g, bp 121-123° C./0.3 mm Hg, 66.8% yield).

Workup

  1. temperaturerefluxed for 2 days
  2. filtrationThe organic mixture is filtered through diatomaceous earth
  3. concentrationconcentrated in vacuo
  4. customto obtain a residue
  5. distillationThe residue is distilled

Sources & evidence

ORD record
ord-c81f382a058a4d85a0dbc316df7b7674
Source dataset
uspto-grants-2001_05
Patent number
US06235754B1

Reaction notes

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