Carbon tetrabromide → HCID 131721609, compound

HRID 850232Notes

Reaction equation

HRID 850232 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][SiH2:11][C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14][CH3:15])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:37](Br)(Br)([Br:39])[Br:38]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([O:10][SiH2:11][C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14][CH3:15])[CH:7]=[CH:6][C:3]=1[CH:4]=[C:37]([Br:39])[Br:38]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 131721610HCID 131721610, compound

Product 1

HCID 131721609HCID 131721609, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 26 mmol of 2-fluoro-4-dimethylbutylsilyloxy benzaldehyde in 50 ml of methylene chloride were added dropwise under ice-cooling 110 mmol of triphenyl phosphine and 52 mmol of carbon tetrabromide and the solution was stirred at the same temperature for one hour. The insoluble matter was removed from the reaction solution which was concentrated under reduced pressure to provide a yellow oily product. Purification of the product by a silica gel column chromatography gave 26 mmol of 2-fluoro-4-dimethylbutylsilyloxyphenyl-2,2-dibromoethylene as a colourless oily product.

Workup

  1. customThe insoluble matter was removed from the reaction solution which
  2. concentrationwas concentrated under reduced pressure
  3. customto provide a yellow oily product
  4. customPurification of the product by a silica gel column chromatography

Sources & evidence

ORD record
ord-1b1bc3d3ce5946979e6fddec8d18c63c
Source dataset
uspto-grants-2000_01
Patent number
US06017467

Reaction notes

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