Sulfuryl chloride → 3-Bromo-5-chloro-2,6-dimethoxybenzoic acid

HRID 224419

Reaction equation

HRID 224419 reaction equation
S(Cl)([Cl:4])(=O)=O.[Br:6][C:7]1[C:8]([O:18][CH3:19])=[C:9]([C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11]>C(Cl)(Cl)Cl>[Br:6][C:7]1[C:8]([O:18][CH3:19])=[C:9]([C:13]([O:16][CH3:17])=[C:14]([Cl:4])[CH:15]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 27747443-Bromo-2,6-dimethoxybenzoic acid

Product 1

HCID 28004633-Bromo-5-chloro-2,6-dimethoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 40 ml (0.5 mol) of sulphuryl chloride in 100 ml of chloroform is added dropwise to a solution of 26.1 g (0.1 mol) of 3-bromo-2,6-dimethoxybenzoic acid in 150 ml of chloroform. After a night at room temperature the solution is refluxed for 45 minutes. The solvent is evaporated and the residue recrystallized from isopropyl ether - light petroleum. Yield: 23.5 g, m.p. 98.5°-100° C.

Workup

  1. customThe solvent is evaporated
  2. customthe residue recrystallized from isopropyl ether - light petroleum

Sources & evidence

ORD record
ord-a0df755bb7b74005aa58054f65e99638
Source dataset
uspto-grants-1980_11
Patent number
US04232037

Linked notes

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