Water → 2-Bromo-5-((R)-3-methanesulfonyl-2-methyl-propoxy)-1,3-dimethyl-benzene

HRID 237502Notes

Reaction equation

HRID 237502 reaction equation
[Br:1][C:2]1[C:17]([CH3:18])=[CH:16][C:5]([O:6][CH2:7][C@@H:8]([CH3:15])[CH2:9]OS(C)(=O)=O)=[CH:4][C:3]=1[CH3:19].[CH3:20][S:21]([O-:23])=[O:22].[Na+].O>CN(C)C=O>[Br:1][C:2]1[C:3]([CH3:19])=[CH:4][C:5]([O:6][CH2:7][C@@H:8]([CH3:15])[CH2:9][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:16][C:17]=1[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 2733271Sodium methanesulfinateHCID 86697162Methanesulfonic acid (R)-3-(4-bromo-3,5-dimethyl-phenoxy)-2-methyl-propyl ester

Product 1

HCID 866971632-Bromo-5-((R)-3-methanesulfonyl-2-methyl-propoxy)-1,3-dimethyl-benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methanesulfonic acid (R)-3-(4-bromo-3,5-dimethyl-phenoxy)-2-methyl-propyl ester (148 mg) and sodium methanesulfinate (215 mg) are stirred in 3 mL of N,N-dimethylformamide at 80° C. for 4 h. The reaction mixture is cooled to room temperature, water is added and the reaction mixture is extracted with diethyl ether. The organic phase is separated, dried over sodium sulfate and concentrated under vacuum to give the title compound. Yield: 118 mg.

Workup

  1. extractionthe reaction mixture is extracted with diethyl ether
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6ae3a5f8ec88425bad1355cc7f0e7a6d
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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