N-bromobutanimide → Methyl 3-bromo-4-cyclopropylbenzoate

HRID 1487854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1487854
[CH:1]1([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[Br:14]N1C(=O)CCC1=O>FC(F)(F)C(O)=O>[Br:14][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:4]=1[CH:1]1[CH2:2][CH2:3]1)[C:8]([O:10][CH3:11])=[O:9]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 11658370Methyl 4-cyclopropylbenzoate2×

Produkt 1

HCID 44828964Methyl 3-bromo-4-cyclopropylbenzoateAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Into a 50-mL round-bottom flask, was placed a mixture of methyl 4-cyclopropylbenzoate (compound 10.1, 500 mg, 2.84 mmol), N-bromosuccinimide (500 mg, 2.81 mmol) and trifluoroacetic acid (20 mL). The mixture was stirred overnight at 50° C., then cooled and carefully quenched with water (10 mL). The mixture was extracted with ethyl acetate (3×30 mL) and the combined organic layers were washed with brine (3×30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether as the eluent to yield 0.5 g (69%) of the title compound as a yellow oil.

Aufarbeitung

  1. customInto a 50-mL round-bottom flask, was placed
  2. temperaturecooled
  3. customcarefully quenched with water (10 mL)
  4. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  5. washthe combined organic layers were washed with brine (3×30 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography with petroleum ether as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-07c138283826418a84107e03cd42dbd0
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428502B2

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