Bromine → HCID 86644709, Verbindung

HRID 1097535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097535
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([NH:20][C:21](=[O:33])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[S-:34][C:35]#[N:36].[K+].BrBr>C(O)(=O)C>[NH2:36][C:35]1[S:34][C:11]2[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([O:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([NH:20][C:21](=[O:33])[CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=4)[CH:14]=3)[CH:4]=[CH:3][C:2]=2[N:1]=1

Komponenten

5

Edukt 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 66810289HCID 66810289, Verbindung

Produkt 1

HCID 86644709HCID 86644709, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

To a solution of methyl 5-amino-2-[4-fluoro-3-({[3-(trifluoromethyl)phenyl]acetyl}amino)phenoxy]benzoate (3.00 g, 6.09 mmol) in acetic acid (70 mL) was added potassium thiocyanate (2.37 g, 24.4 mmol), and the mixture was stirred at room temperature for 10 min. A solution of bromine (1.27 mg, 7.92 mmol) in acetic acid (35 mL) was added dropwise to the obtained solution over 20 min. After the completion of the dropwise addition, the mixture was stirred at room temperature for 36 hr. Insoluble material was filtered off and washed with ethyl acetate (200 mL). The filtrate and washings were combined and the mixture was concentrated under reduced pressure. The obtained residue was suspended in ethyl acetate (100 mL), and the suspension was washed successively with saturated aqueous sodium hydrogen carbonate solution (2×100 mL) and saturated brine (100 mL), and dried over anhydrous magnesium sulfate. Insoluble material was filtered off, the filtrate was purified by basic silica gel column chromatography (eluate: ethyl acetate), and the obtained solution was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate/n-hexane (1:1) to give the title compound (2.78 g, 88%) as a white powder.

Aufarbeitung

  1. additionAfter the completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature for 36 hr
  3. filtrationInsoluble material was filtered off
  4. washwashed with ethyl acetate (200 mL)
  5. concentrationthe mixture was concentrated under reduced pressure
  6. washthe suspension was washed successively with saturated aqueous sodium hydrogen carbonate solution (2×100 mL) and saturated brine (100 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationInsoluble material was filtered off
  9. customthe filtrate was purified by basic silica gel column chromatography (eluate: ethyl acetate)
  10. concentrationthe obtained solution was concentrated under reduced pressure
  11. customThe obtained residue was recrystallized from ethyl acetate/n-hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-9bf178237f584a368dab202a0efe1646
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143258B2

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