Hydrogen Bromide → Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetate

HRID 381321Notes

Reaction equation

HRID 381321 reaction equation
[BrH:1].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11](O)[C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:5]=2[O:4][CH2:3]1>C1(C)C=CC=CC=1>[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]([Br:1])[C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 273389Methyl 2-(benzo[d][1,3]dioxol-5-yl)-2-hydroxyacetate

Product 1

HCID 11821769Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Hydrobromic acid (20 ml of 62%w/v solution in water) was added to methyl 2-(1,3-benzodioxol-5-yl)-2-hydroxyacetate (from step (b), 11 g, 52 mmol) in toluene (200 ml). After stirring for 3 hours the aqueous layer was removed and the organic layer was evaporated in vacuo. The residue was flash chromatographed, eluting with dichloromethane, and then crystallised with diisopropylether and hexane.

Workup

  1. customwas removed
  2. customthe organic layer was evaporated in vacuo
  3. customchromatographed
  4. washeluting with dichloromethane
  5. customcrystallised with diisopropylether and hexane

Sources & evidence

ORD record
ord-79592c0b822548a281dd4b48267eafd5
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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