Phosphorus tribromide → 5-(Bromomethyl)-6-chloro-2H-1,3-benzodioxole

HRID 906490Notes

Reaction equation

HRID 906490 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([Cl:12])[C:8]([CH2:10]O)=[CH:9][C:3]=2[O:2]1.P(Br)(Br)[Br:14]>C(OCC)C>[Br:14][CH2:10][C:8]1[C:7]([Cl:12])=[CH:6][C:4]2[O:5][CH2:1][O:2][C:3]=2[CH:9]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 7015319(6-Chloro-1,3-benzodioxol-5-yl)methanol

Product 1

HCID 191052995-(Bromomethyl)-6-chloro-2H-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

2.5 g of 6-chloropiperonyl alcohol are dissolved in 80 ml of ethyl ether. The solution is cooled to 0° C. and then 1.9 ml of PBr3 are added. The mixture is stirred at ambient temperature for 18 hours. It is poured onto ice and then extraction is carried out with AcOEt. The organic phase is washed with a saturated NaCl solution. 3.3 g of powder are obtained.

Workup

  1. additionIt is poured onto ice
  2. extractionextraction
  3. washThe organic phase is washed with a saturated NaCl solution

Sources & evidence

ORD record
ord-758596f7645c4ff1b89bab180b65290d
Source dataset
uspto-grants-2011_09
Patent number
US08012991B2

Reaction notes

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