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

HRID 514709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514709
[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]

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 70976499HCID 70976499, Verbindung

Produkt 1

HCID 867296143-Fluoro-5-[(methylsulfonyl)methyl]anilineAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10313229titanium(III) trichlorideKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Titanium(III)chloride solution (about 15%) in about 10% hydrochloric acid (29 mL, Merck Schuchardt OHG) 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/ethyl acetate 1:1 to ethyl acetate) to give the desired product (262 mg; 1.29 mmol).

Aufarbeitung

  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/ethyl acetate 1:1 to ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-596b7721ab6840bea4c3a49fcc47f217
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108926B2

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