Methanol → 4-[4-Bromo-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-benzoic acid

HRID 69396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69396
C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]([Br:16])[C:14]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[O:13][N:12]=2)=[CH:7][C:6]=1[CH3:29])C.O.[OH-].[Li+].CO>O>[Br:16][CH:15]1[C:14]([C:21]2[CH:22]=[C:23]([Cl:28])[CH:24]=[C:25]([Cl:27])[CH:26]=2)([C:17]([F:18])([F:19])[F:20])[O:13][N:12]=[C:11]1[C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:30])=[O:3])=[C:6]([CH3:29])[CH:7]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 866551484-[4-Bromo-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid ethyl ester

Produkt 1

HCID 866551474-[4-Bromo-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-benzoic acidAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-[4-bromo-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid ethyl ester (0.71 g, 1.35 mmol) (Example 1.6), lithium hydroxide monohydrate (0.17 g, 4 mmol), methanol (25 ml) and water (5 ml) was stirred at ambient temperature for 60 hours. The mixture was concentrated and the residue dissolved in water. The solution was acidified by addition of aqueous hydrochloric acid (1N). The precipitate was isolated by filtration and dried under vacuum to afford 4-[4-bromo-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-benzoic acid (0.59 g, 88% yield) as a white powder. 1H-NMR (CDCl3, 400 MHz): 8.05-7.45 (m, 6H), 5.87 (s, 1H), 2.65 (s, 3H) ppm.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue dissolved in water
  3. additionThe solution was acidified by addition of aqueous hydrochloric acid (1N)
  4. customThe precipitate was isolated by filtration
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e2c8185aced54ac89e8c7a80aed00b8b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822502B2

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