Phosphorus tribromide → HCID 19844235, compound

HRID 34709Notes

Reaction equation

HRID 34709 reaction equation
[CH2:1]([C:5]1[CH2:6][C:7]2[C:12]([C:13]=1OC)=[CH:11][C:10]1[O:16][CH2:17][O:18][C:9]=1[CH:8]=2)[CH2:2][CH2:3][CH3:4].P(Br)(Br)[Br:20]>C(Cl)(Cl)Cl>[CH2:1]([C:5]1[CH2:6][C:7]2[C:12]([C:13]=1[Br:20])=[CH:11][C:10]1[O:16][CH2:17][O:18][C:9]=1[CH:8]=2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 198442392-n-Butyl-3-methoxy-5,6-methylenedioxyindene

Product 1

HCID 19844235HCID 19844235, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolved in 100 ml of chloroform was 9.3 g of 2-n-butyl-3-methoxy-5,6-methylenedioxyindene, followed by a dropwise addition of 15.4 g of phosphorus tribromide over 1 hour under ice cooling. After stirring the resultant mixture for further 4 hours, the reaction mixture was stirred for additional 4 hours at room temperature. The reaction mixture was washed with water, a 5% aqueous solution of sodium hydroxide and water successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: a 20:1 mixture of n-hexane and ether) to give 7.6 g of 2-n-butyl-3-bromo-5,6-methylenedioxyindene having a melting point of 63.0°-64.0° C. as crystals (yield: 68%).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materiala 5% aqueous solution of sodium hydroxide and water successively, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (eluent
  5. additiona 20:1 mixture of n-hexane and ether)

Sources & evidence

ORD record
ord-ada1fce3694045b5954ca4e93eb682d9
Source dataset
uspto-grants-1988_08
Patent number
US04762927

Reaction notes

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