Sodium Hydroxide → 3-Fluoro-5-[(methylsulfonyl)methyl]aniline

HRID 1405179Notes

Reaction equation

HRID 1405179 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:3]=1.[OH-].[Na+]>Cl.C1COCC1.[Cl-].[Ti+3].[Cl-].[Cl-]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:3]=1)[NH2:8]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 70976499HCID 70976499, compound

Product 1

HCID 867296143-Fluoro-5-[(methylsulfonyl)methyl]anilineYield 30.1%

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Titanium(III)chloride solution (about 15%) in about 10% hydrochloric acid (MERCK (MDA) INCL SCHUCHARDT; 29 ml) was added to a stirred solution of crude 1-fluoro-3-[(methylsulfonyl)methyl]-5-nitrobenzene (1.00 g) in THF (45 ml) at room temperature and the batch was stirred for 16 hours. The batch was cooled with an ice bath while 1N sodium hydroxide solution was added to raise the pH value of the reaction mixture to 8-9. It was stirred for 30 minutes at this temperature before the batch was extracted with ethyl acetate (2×). The combined organic phases were washed with brine, filtered using a Whatman filter and concentrated. The residue was purified by column chromatography (hexane/ethlyacetate 1:1 to ethyl acetate) to give the desired product (262 mg; 1.29 mmol)

Workup

  1. additionwas added
  2. temperatureto raise the pH value of the reaction mixture to 8-9
  3. stirringIt was stirred for 30 minutes at this temperature before the batch
  4. extractionwas extracted with ethyl acetate (2×)
  5. washThe combined organic phases were washed with brine
  6. filtrationfiltered
  7. filtrationfilter
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (hexane/ethlyacetate 1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-2c71ad070ea6431ebce99698c31b081d
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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