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

HRID 1835300Notes

Reaction equation

HRID 1835300 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-4d767a9bf4cb419fa7ec9b19b5a71dac
Source dataset
uspto-grants-2004_08
Patent number
US06770658B2

Reaction notes

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