Water → 6-(2-Bromoacetyl)-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17337

Reaktionsgleichung

Reaktionsgleichung von HRID 17337
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:20]#[N:21])[C:10]([CH3:19])=[C:11]([C:14]([O:16]CC)=[CH2:15])[C:12]=3[F:13])[N:8]=2)[CH2:3][CH2:2]1.O.[Br:23]N1C(=O)CCC1=O>O1CCCC1>[Br:23][CH2:16][C:14]([C:11]1[C:12]([F:13])=[C:6]2[O:5][C:4]([CH:1]3[CH2:3][CH2:2]3)=[N:8][C:7]2=[C:9]([C:20]#[N:21])[C:10]=1[CH3:19])=[O:15]

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 685864422-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 866308356-(2-Bromoacetyl)-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrileAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-78) (9.34 g, 30.1 mmol) was dissolved in tetrahydrofuran (450 ml), then water (27 ml) and N-bromosuccinimide (5.73 g, 31.58 mmol) were added all at a time, followed by stirring at room temperature for 45 minutes. After the reaction, the solvent was evaporated away under reduced pressure, followed by dilution with ethyl acetate and by washing with aqueous sodium thiosulfate solution and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography and eluted with a mixed solvent of n-hexane/ethyl acetate (4:1, v/v) to obtain the intended product (9.63 g, 95%) as a white solid.

Aufarbeitung

  1. customAfter the reaction
  2. customthe solvent was evaporated away under reduced pressure
  3. washby washing with aqueous sodium thiosulfate solution and saturated brine
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. washeluted with a mixed solvent of n-hexane/ethyl acetate (4:1

Quellen und Nachweise

ORD-Eintrag
ord-8b0207fc297d40fb8d9dc26985d7f16b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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