Hexane → N-(2-Bromo-5-fluorophenyl)pivalamide

HRID 712165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712165
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].CCCCCC>C(Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH:4][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 27733172-Bromo-5-fluoroaniline

Produkt 1

HCID 59731998N-(2-Bromo-5-fluorophenyl)pivalamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cold solution of 2-bromo-5-fluoroaniline (50.0 g, 263.14 mmol) in DCM (400 mL) was added triethyl amine (48.0 mL, 342.10 mmol). The resulting mixture was stirred at 0° C. for 10 min followed by addition of pivaloyl chloride (36.0 mL, 289.50 mmol) then stirred at rt for 3 h. After completion of reaction (by TLC), the reaction mixture was diluted with DCM and washed with saturated solution of NaHCO3. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 1.0% EtOAc:hexane to obtain the product as an off white solid (66.0 g, 92% yield).

Aufarbeitung

  1. stirringthen stirred at rt for 3 h
  2. customAfter completion of reaction (by TLC)
  3. washwashed with saturated solution of NaHCO3
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified over 100-200 M silica-gel

Quellen und Nachweise

ORD-Eintrag
ord-40b1b2b87e1744fa85dbed8f2ed8857b
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

Notizen zur Reaktion

Wird geladen…