Water → 6-Hydroxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

HRID 556355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 556355
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]3[CH:16]=[CH:17][C:18]([O:20]C)=[CH:19][C:14]=3[S:13][N:12]=2)=[O:10])=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].B(Br)(Br)Br.O.CCOC(C)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:15]3[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:14]=3[S:13][N:12]=2)=[O:10])=[CH:4][C:3]=1[C:22]([F:24])([F:23])[F:25]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 669929426-Methoxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

Produkt 1

HCID 1363466286-Hydroxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A suspension of 252 mg (0.68 mMol) 6-methoxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide in 15 ml CH2Cl2 is cooled in an ice-bath, then 20 ml of a 1 M solution of BBr3 in CH2Cl2 are added. The suspension is stirred for 3 days at 45° C., the resulting solution is cooled, poured into water and EtOAc, the aq. layer is separated off and extracted twice with EtOAc. The organic layers are washed twice with water and sat. NaHCO3, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; acetone/hexane 1:95→2:3) gives the title compound: MS: [M−1]=355; TLC(hexane/acetone 2:1): Rf=0.46.

Aufarbeitung

  1. temperatureis cooled in an ice-bath
  2. temperaturethe resulting solution is cooled
  3. customthe aq. layer is separated off
  4. extractionextracted twice with EtOAc
  5. washThe organic layers are washed twice with water and sat. NaHCO3
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dafc320054874d4db0ccd81830b58111
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058276B2

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