Piperonyl alcohol → 1,3-Benzodioxole, 5-(bromomethyl)-

HRID 990118Notes

Reaction equation

HRID 990118 reaction equation
[CH2:1](O)[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.P(Br)(Br)[Br:13]>C(OCC)C>[CH2:1]([Br:13])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 10322Piperonyl alcoholHCID 24614Phosphorus tribromide

Product 1

HCID 64514231,3-Benzodioxole, 5-(bromomethyl)-Yield 182%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of piperonyl alcohol (5.0 g, 32.86 mmol) in anhydrous diethyl ether (80 mL) was added PBr3 (1.56 mL, 16.43 mmol) in one portion, and the resulting mixture was stirred at room temperature for 3 hours. The mixture was diluted with diethyl ether (100 mL) and washed with H2O (2×50 mL), saturated NaHCO3 (2×50 mL), and brine (2×50 mL). The ether layer was dried over anhydrous MgSO4, and the solvent was removed under reduced pressure to afford piperonyl bromide (6.43 g, 91%) as a yellow-grey solid.

Workup

  1. washwashed with H2O (2×50 mL), saturated NaHCO3 (2×50 mL), and brine (2×50 mL)
  2. dry with materialThe ether layer was dried over anhydrous MgSO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-74c4b8e1b676453ab76b3e6ac6b94f5b
Source dataset
uspto-grants-2002_10
Patent number
US06458829B1

Reaction notes

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