1-Bromo-4-fluorobenzene → Tert-butyl 3-(4-bromophenoxy)azetidine-1-carboxylate

HRID 2384940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384940
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11](F)=[CH:10][CH:9]=1.[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24]([OH:26])[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24]([O:26][C:11]2[CH:12]=[CH:13][C:8]([Br:7])=[CH:9][CH:10]=2)[CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Komponenten

5

Edukt 3

HCID 99931-Bromo-4-fluorobenzeneHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 68605010Tert-butyl 3-(4-bromophenoxy)azetidine-1-carboxylateAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Add dropwise potassium tert-butoxide in THF (34.6 mL, 34.6 mmol) to a solution of p-bromofluorobenzene (6.1 g, 34.6 mmol) in THF (144 mL) and 3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (5.0 g, 28.9 mmol) at RT. Heat the mixture at 70° C. overnight. Cool the mixture to RT, quench with water, dilute with Et2O, and wash once with saturated NH4Cl. Back extract the aqueous with Et2O, dry the combined organics over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, eluting with 25% EtOAc/hexane to give 4.4 g (46%) of the title compound. LC-MS/ES m/z (81Br) 274 [M−tertBu+H]+.

Aufarbeitung

  1. temperatureCool the mixture to RT
  2. customquench with water
  3. additiondilute with Et2O
  4. washwash once with saturated NH4Cl
  5. extractionBack extract the aqueous with Et2O
  6. dry with materialdry the combined organics over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the crude material by flash chromatography
  10. washeluting with 25% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-fade022164b841bd8f73f8282fd72965
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263772B2

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