Carbon Dioxide → Benzoic acid, 2-(methylthio)-4-(trifluoromethyl)-

HRID 21461

Reaktionsgleichung

Reaktionsgleichung von HRID 21461
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[S:17][CH3:18].[C:19](=[O:21])=[O:20].Cl>CCOCC>[CH3:18][S:17][C:8]1[CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=[CH:12][C:7]=1[C:19]([OH:21])=[O:20]

Komponenten

6

Edukt 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 11000144Benzene, 1-bromo-2-(methylthio)-4-(trifluoromethyl)-HCID 178418339Butyllithium

Produkt 1

HCID 11085762Benzoic acid, 2-(methylthio)-4-(trifluoromethyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

n-Butyllithium (2.5M in hexane, 25 ml) was added under an inert atmosphere to a stirred solution of 4-bromo-3-(methylsulphenyl)benzotrifluoride (16.4 g) in ether maintaining the temperature below -70° C. for 2 hours. The mixture was poured onto solid carbon dioxide pellets, stirred for 10 rains and aqueous hydrochloric acid added. The layers were separated and the aqueous layer was extracted with ether. The combined organic layers were washed with water, dried (MgSO4) and filtered. The filtrate was evaporated and the residue was triturated with cyclohexane and filtered to give 2-(methylsulphenyl)-4-trifluoromethylbenzoic acid (12.4 g) as a white solid NMR (CDCl3 +DMSO-d6): 2.45 (s,3H), 7.2(d,1H), 7.3(s,1H), 8.0(d,1H), 10.7-11(bs,1H).

Aufarbeitung

  1. additionadded
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ether
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customthe residue was triturated with cyclohexane
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-4b763ab9c11f46fdbe59706e9ea487f7
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424276

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