Butyl bromide → Butyl 4-bromo-3-(butyloxy)benzoate

HRID 2098893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098893
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][CH2:20][CH2:21][CH3:22]>CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:19][CH2:20][CH2:21][CH3:22])=[O:7])=[CH:4][C:3]=1[O:11][CH2:10][CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 3

HCID 8002Butyl bromideHCID 10796Cesium carbonateHCID 64209734-Bromo-3-hydroxybenzoic acid

Produkt 1

HCID 57467609Butyl 4-bromo-3-(butyloxy)benzoateAusbeute 66,81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a flask containing 4-bromo-3-hydroxybenzoic acid (D.1) (available from Combi-Blocks Inc.) (2.40 g, 11.06 mmol) and cesium carbonate (8.287 g, 25.44 mmol) in DMF (40 mL), was added 1-bromobutane (2.494 mL, 23.22 mmol), and the mixture was stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by CombiFlash® chromatography (0 to 20% EtOAc/hexanes) to provide D.2 (2.4326 g, 66.81% yield).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by CombiFlash® chromatography (0 to 20% EtOAc/hexanes)
  7. customto provide D.2 (2.4326 g, 66.81% yield)

Quellen und Nachweise

ORD-Eintrag
ord-68808c05ec394b43bcee50df20da8fa2
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450522B2

Notizen zur Reaktion

Wird geladen…