Water → 5-(3-Bromopropyl)-1,3-dioxaindane

HRID 1093345Notes

Reaction equation

HRID 1093345 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH2:12]O)=[CH:4][C:3]=2[O:2]1.P(Br)(Br)[Br:15].O>C(OCC)C>[Br:15][CH2:12][CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 110304141,3-Benzodioxole-5-propanol

Product 1

HCID 127122875-(3-Bromopropyl)-1,3-dioxaindane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 21-1 (9.72 g) was dissolved in diethyl ether (100 ml), phosphorus tribromide (5.27 ml) was added under ice-cooling, and the mixture was stirred under ice-cooling for 6.5 hr. To the reaction mixture was slowly added water was added, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (5.05 g) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 6.5 hr
  3. additionwas added
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f5a2b9c672024ec7a735921bd75117e6
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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