Water → HCID 89444094, Verbindung

HRID 1771737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771737
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.O=S(Cl)Cl.[NH2:22][C:23]1[C:24]([F:32])=[C:25]([OH:31])[CH:26]=[C:27]([CH3:30])[C:28]=1[F:29].O>C(Cl)Cl.CN(C=O)C.C1COCC1>[F:32][C:24]1[C:25]([OH:31])=[CH:26][C:27]([CH3:30])=[C:28]([F:29])[C:23]=1[NH:22][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:9]=[CH:10][C:2]=1[F:1]

Komponenten

8

Edukt 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 463123323',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acidHCID 894437823-Amino-2,4-difluoro-5-methylphenol

Produkt 1

HCID 89444094HCID 89444094, VerbindungAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-fluoro-5-(3-fluorophenyl)benzoic acid (Intermediate III(a)) (437 mg, 1.87 mmol, 1.1 eq) in CH2Cl2 (10 mL) and DMF (3 drops) was added SOCl2 (15 mL) dropwise at 0° C. The solution was stirred at room temperature for 1 h, then concentrated in vacuo. The residue obtained was dissolved in THF (20 mL) and added dropwise to a solution of 3-amino-2,4-difluoro-5-methyl-phenol (270 mg, 1.70 mmol, 1.0 eq) in THF (10 mL) at 0° C. After addition was completed, the reaction mixture was stirred at room temperature for 2 h, then poured into water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether: EtOAc, 10:1 to 3:1) to give the title compound as a white solid (285 mg, 45%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. additionAfter addition
  4. stirringthe reaction mixture was stirred at room temperature for 2 h
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue obtained
  11. customwas purified by column chromatography (petroleum ether: EtOAc, 10:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-552f183a47ca4dfa8a57912769315f05
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249085B2

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