Carbon tetrabromide → 1-(2,2-dibromovinyl)-4-methoxybenzene

HRID 736853Notes

Reaction equation

HRID 736853 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29][CH:28]=1>>[Br:21][C:20]([Br:24])=[CH:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 312444-Methoxybenzaldehyde

Product 1

HCID 108592781-(2,2-dibromovinyl)-4-methoxybenzeneYield 99.9%

Procedure

Triphenylphosphine (57.8 g, 220 mmol) was dissolved in dichromomethane (200 ml) in nitrogen atmosphere, and carbon tetrabromide (36.5 g, 110 mmol) was added little by little under cooling with ice, followed by stirring for 30 minutes. Then, p-anisic aldehyde (10.0 g, 73.4 mmol) was dropwise added under cooling with ice, followed by stirring for 10 minutes. The reaction solution was subjected to filtration, silica gel (50 g) was added to the filtrate, and the filtrate was concentrated under reduced pressure to dryness, and the resulting product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give the desired compound 1-(2,2-dibromovinyl)-4-methoxybenzene (21.4 g, quant.) as pale yellow solid.

Workup

  1. additionwas added little by little
  2. temperatureunder cooling with ice
  3. temperatureunder cooling with ice
  4. stirringby stirring for 10 minutes
  5. filtrationThe reaction solution was subjected to filtration, silica gel (50 g)
  6. additionwas added to the filtrate
  7. concentrationthe filtrate was concentrated under reduced pressure to dryness
  8. customthe resulting product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-5f8379ae115a4d40af49f9467ecb509a
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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