Hydrochloric Acid → HCID 58237059, compound

HRID 1188897Notes

Reaction equation

HRID 1188897 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.[OH-:15].[Na+].Cl>CS(C)=O>[CH3:13][CH:12]([O:11][C:4]1[CH:3]=[C:2]([OH:15])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 106318324-Fluoro-2-isopropoxy-1-nitrobenzene

Product 1

HCID 58237059HCID 58237059, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-fluoro-2-(1-methylethoxy)-1-nitrobenzene (20.34 g) in dimethylsulfoxide (150 mL) was added 20% aqueous sodium hydroxide solution (68 mL) at room temperature and the mixture was stirred at 60° C. for 3 h. The mixture was cooled to room temperature and 6M hydrochloric acid (50 mL) was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual oil was solidified with hexane to give the title compound (14.94 g, 74%) as a yellow solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6bcc228ab6bc4dbd8526c6fbbf711012
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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