Carbon tetrabromide → HCID 18975515, compound

HRID 2393293Notes

Reaction equation

HRID 2393293 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:25][C:26]1[CH:27]=[C:28]2[O:36][CH2:35][O:34][C:29]2=[C:30]([CH:33]=1)[CH:31]=O>C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:31][C:30]1[CH:33]=[C:26]([Br:25])[CH:27]=[C:28]2[O:36][CH2:35][O:34][C:29]=12

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 125140976-Bromo-2H-1,3-benzodioxole-4-carbaldehyde

Product 1

HCID 18975515HCID 18975515, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Carbon tetrabromide (44.3 g, 0.134 mol) was added portionwise to a solution of triphenylphosphine (70.1 g, 0.267 mol) in methylene chloride (200 ml) under ice cooling. A solution of 5-bromo-2,3-methylenedioxybenzaldehyde (27.65 g, 0.121 mol) in methylene chloride (100 ml) was then added dropwise to the mixture over 20 minutes. The reaction mixture was stirred at room temperature for 2 hours, washed with water and with saturated aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was added with ethyl acetate (200 ml), and the mixture was heated to 60° C. and then added with hexane (50 ml). The mixture was cooled to room temperature, and the deposited triphenylphosphine oxide was removed by filtration and the filtrate was concentrated. Triphenylphosphine oxide was removed again in a similar manner by using 100 ml of ethyl acetate and 100 ml of hexane, and the filtrate was concentrated. The residue was purified by silica gel chromatography (Wako Gell C-300: 200 g, eluent: hexane/ethyl acetate=1/10) to give β,β-dibromo-5-bromo-2,3-methylenedioxystyrene (42.36 g).

Workup

  1. washwashed with water and with saturated aqueous sodium hydrogen carbonate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. additionThe residue was added with ethyl acetate (200 ml)
  5. temperaturethe mixture was heated to 60° C.
  6. additionadded with hexane (50 ml)
  7. temperatureThe mixture was cooled to room temperature
  8. customthe deposited triphenylphosphine oxide was removed by filtration
  9. concentrationthe filtrate was concentrated
  10. customTriphenylphosphine oxide was removed again in a similar manner
  11. concentrationthe filtrate was concentrated
  12. customThe residue was purified by silica gel chromatography (Wako Gell C-300: 200 g, eluent: hexane/ethyl acetate=1/10)

Sources & evidence

ORD record
ord-72691810bf8245bdba28eb38f47fbea9
Source dataset
uspto-grants-1998_09
Patent number
US05807860

Reaction notes

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