4-Chlorobenzaldehyde → 1-Chloro-4-(2,2-dibromoethenyl)benzene

HRID 1392772Notes

Reaction equation

HRID 1392772 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10](Br)(Br)([Br:12])[Br:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:10]([Br:12])[Br:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Product 1

HCID 64229811-Chloro-4-(2,2-dibromoethenyl)benzeneYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chlorobenzaldehyde (2.81 g) was dissolved in methylene chloride (300 ml), and carbon tetrabromide (13.3 g) and triphenylphosphine (21.0 g) were added to stir the mixture at room temperature for 90 minutes. After insoluble matter deposited was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1) to obtain the title compound (5.54 g).

Workup

  1. customAfter insoluble matter deposited was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-038ee91b26fd4cf682b70a022739b592
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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