Carbon tetrabromide → HCID 21466283, compound

HRID 1940242Notes

Reaction equation

HRID 1940242 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[Br:25][C:26]1[CH:35]=[C:34]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=2)[CH:33]=[CH:32][C:27]=1[O:28][CH2:29][CH:30]=O>C(Cl)Cl.[Zn]>[Br:25][C:26]1[CH:35]=[C:34]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=2)[CH:33]=[CH:32][C:27]=1[O:28][CH2:29][CH:30]=[C:20]([Br:24])[Br:21]

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53993559HCID 53993559, compound

Product 1

HCID 21466283HCID 21466283, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent2×

Procedure

First, 0.38 g of zinc dust, 1.54 g of triphenylphosphine, 1.94 g of carbon tetrabromide and 20 ml of methylene chloride were charged into a reaction vessel, and stirred at room temperature. After 24 hours, a solution prepared by dissolving 1.0 g of (2-bromo-4-(3-chlorophenoxy) phenoxy)acetaldehyde in 5 ml of methylene chloride was added dropwise to the solution with stirring. After stirring at room temperature for 6 hours, the reaction solution was concentrated to give a residue. This residue was subjected to silica gel column chromatography to give 0.48 g of 2-bromo-4-(3-chlorophenoxy)-1-(3,3-dibromo-2-propenyloxy)benzene, yield 33%; nD24.0 1.6282.

Workup

  1. customa solution prepared
  2. additionwas added dropwise to the solution
  3. stirringwith stirring
  4. stirringAfter stirring at room temperature for 6 hours
  5. concentrationthe reaction solution was concentrated
  6. customto give a residue

Sources & evidence

ORD record
ord-224edd3a2453487094e0db4f5dd0fb77
Source dataset
uspto-grants-1997_12
Patent number
US05698702

Reaction notes

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