Phenol → 2-(2-Fluoro-4-phenoxy-benzyloxy)-tetrahydro-pyran

HRID 2041339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2041339
Br[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)=[C:4]([F:16])[CH:3]=1.[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]Cl.CN1C(=O)CCC1>[F:16][C:4]1[CH:3]=[C:2]([O:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][C:5]=1[CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1

Komponenten

7

Edukt 4

HCID 996PhenolHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 576563392-(4-Bromo-2-fluorobenzyloxy)-tetrahydropyran

Produkt 1

HCID 576563912-(2-Fluoro-4-phenoxy-benzyloxy)-tetrahydro-pyranAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Mix under argon atmosphere 2-(4-bromo-2-fluorobenzyloxy)-tetrahydropyran (2.9 g, 10 mmol), phenol (1.9 g, 20 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (184.3 mg, 1.0 mmol), cesium carbonate (6.5 g, 20 mmol) and anhydrous NMP (20 mL). Degas the flask and fill with argon: Add copper(I) chloride (495 mg, 5 mmol) quickly. Degas the flask three times then fill with argon. Heat at 120° C. for 3 h. Cool to ambient temperature. Dilute with EtOAc and filter. Concentrate in vacuo and purify by chromatography on silica gel to obtain the desired intermediate (2.05 g, 68%). MS (ES+) m/z: 325 (M+Na)+.

Aufarbeitung

  1. customDegas the flask
  2. customDegas the flask three times
  3. temperatureCool to ambient temperature
  4. additionDilute with EtOAc
  5. filtrationfilter
  6. concentrationConcentrate in vacuo
  7. custompurify by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-324a01ac3fac452484d246faae2cd138
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580780B2

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