Water → Methyl 5-(4-t-Butylphenyldithio)-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3-pyridinecarboxylate

HRID 395400

Reaktionsgleichung

Reaktionsgleichung von HRID 395400
[F:1][CH:2]([F:22])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([SH:17])=[C:5]([C:18]([F:21])([F:20])[F:19])[N:4]=1.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([SH:33])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].BrBr.O>C(O)(=O)C>[C:23]([C:27]1[CH:28]=[CH:29][C:30]([S:33][S:17][C:6]2[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:3]([CH:2]([F:1])[F:22])=[N:4][C:5]=2[C:18]([F:21])([F:20])[F:19])=[CH:31][CH:32]=1)([CH3:26])([CH3:24])[CH3:25]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24408BromineHCID 754544-Tert-ButylbenzenethiolHCID 9974711Methyl 2-(difluoromethyl)-4-isobutyl-5-mercapto-6-(trifluoromethyl)-3-pyridinecarboxylate

Produkt 1

HCID 22668800Methyl 5-(4-t-Butylphenyldithio)-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3-pyridinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a mixture of 100 mg of compound 7 and 48.6 mg of 4-t-butylbenzenethiol in 5 ml of acetic acid was added 23 mg of bromine. The reaction mixture was stirred for 1 h, poured into water and extracted with ether. The ether extract was washed with saturated sodium bicarbonate, dried over MgSO4 and concentrated in vacuo. The residue was purified by preparative TLC (9:1 Hexane: EtOAc) on silica gel to give the desired product.

Aufarbeitung

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with saturated sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC (9:1 Hexane: EtOAc) on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6e3bdec5a6c448dbbb9cd9177d23bf3b
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605624B1

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