Thionyl bromide → Methyl 2-bromo-2-(6-chloro-1,3-benzodioxol-5-yl)acetate

HRID 381331Notes

Reaction equation

HRID 381331 reaction equation
S(Br)([Br:3])=O.[Cl:5][C:6]1[C:7]([CH:15](O)[C:16]([O:18][CH3:19])=[O:17])=[CH:8][C:9]2[O:13][CH2:12][O:11][C:10]=2[CH:14]=1>C1(C)C=CC=CC=1>[Br:3][CH:15]([C:7]1[C:6]([Cl:5])=[CH:14][C:10]2[O:11][CH2:12][O:13][C:9]=2[CH:8]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 68176Thionyl bromideHCID 22467215Methyl 2-(6-chloro-1,3-benzodioxol-5-yl)-2-hydroxyacetate

Product 1

HCID 22467204Methyl 2-bromo-2-(6-chloro-1,3-benzodioxol-5-yl)acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl bromide (3.7 ml) was added to a stirred solution of methyl 2-(6-chloro-1,3-benzodioxol-5-yl)-2-hydroxyacetate from step (a) (7.8 g, 32 mmol) in toluene (50 ml) at ambient temperature. After 6 hours the reaction mixture was evaporated in vacuo, and the residue was flash chromatographed using dichloromethane as eluant, followed by crystallisation from diisopropylether to give the subtitle compound (7.6 g).

Workup

  1. customAfter 6 hours the reaction mixture was evaporated in vacuo
  2. customchromatographed
  3. customfollowed by crystallisation from diisopropylether

Sources & evidence

ORD record
ord-c2aaab0d0734440aa05ae78f78c73140
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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