Hydrochloric Acid → 4-Chloro-2-methylsulphonyl-3-(2,2,2-trifluoroethoxy)benzoic acid

HRID 266590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 266590
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])[C:11]=1F.Cl>C1COCC1>[Cl:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])[C:11]=1[O:6][CH2:5][C:4]([F:8])([F:7])[F:3]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 544424304-Chloro-3-fluoro-2-methylsulphonylbenzoic acid

Produkt 1

HCID 545681774-Chloro-2-methylsulphonyl-3-(2,2,2-trifluoroethoxy)benzoic acidAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Sodium hydride (1.05 g of 80% powder) was suspended in THF and to this was added a solution of 2.2,2-trifluoroethanol (1.9 g) in THF, followed by a solution of 4-chloro-3-fluoro-2-methylsulphonylbenzoic acid (4 g) in THF. The resultant mixture was stirred for 2 hours and then acidified with 2M HCl. The mixture was extracted with ether, washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness yielding 4-chloro-2-methylsulphonyl-3-(2,2,2-trifluoroethoxy)benzoic acid (5.26 g) as a whim solid, NMR (DMSO d6) 2.5(s,3H), 4.8(q,2H), 7.5(d, 1H), 8.0(d, 1H).

Aufarbeitung

  1. extractionThe mixture was extracted with ether
  2. washwashed with water
  3. dry with materialdried (anhydrous magnesium sulphate)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2d0321807ba94bc28127b18602a01163
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650533

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