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

HRID 2104405Notes

Reaction equation

HRID 2104405 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 the solution, followed by stirring at room temperature for 90 minutes. After insoluble matter precipitated was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1), to thereby give the title compound (5.54 g).

Workup

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

Sources & evidence

ORD record
ord-c683b2fa3f234b6f9596b2ebe3406160
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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