Water → 1-Bromo-4-methoxy-2-(methylsulfonyl)benzene

HRID 885087

Reaction equation

HRID 885087 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)(=[O:4])=[O:3].O.[Br:14]Br.[OH-].[Na+]>C(O)(=O)C>[Br:14][C:10]1[CH:9]=[CH:8][C:7]([O:11][CH3:12])=[CH:6][C:5]=1[S:2]([CH3:1])(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 2596501-Methoxy-3-(methylsulfonyl)benzene

Product 1

HCID 670929271-Bromo-4-methoxy-2-(methylsulfonyl)benzeneYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

1-Methanesulfonyl-3-methoxy benzene was dissolved in 90 mL glacial acetic acid. 100 mL water was added. A solution of bromine (4.79 g, 30 mmol) in 10 mL acetic acid was added dropwise at 10° C. The stirring was continued at rt for 15 h. The pH of the mixture was adjusted to pH 8 with aqueous NaOH solution, and extracted with EtOAc (3×200 mL) and dried over Na2SO4. The crude compound was purified by column chromatography (SilicaGel 230-400 mesh; 20% EtOAc in hexanes as an eluent) to give 1-bromo-2-methanesulfonyl-4-methoxy benzene (2.4 g, 45%).

Workup

  1. extractionextracted with EtOAc (3×200 mL)
  2. dry with materialdried over Na2SO4
  3. customThe crude compound was purified by column chromatography (SilicaGel 230-400 mesh

Sources & evidence

ORD record
ord-bf125616711440ff91e2f883b41ad8e2
Source dataset
uspto-grants-2012_08
Patent number
US08242144B2

Linked notes

Loading…