Benzyl Bromide → 6-Fluoro-7-benzyloxychroman-4-one

HRID 1003624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003624
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH2:7][CH2:6][C:5]2=[O:13].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:13]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 211866006-fluoro-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Produkt 1

HCID 211865906-Fluoro-7-benzyloxychroman-4-oneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 6-fluoro-7-hydroxychroman-4-one (the compound of Preparation 29, 0.93 g, 5.11 mmol), benzyl bromide (0.61 mL, 5.13 mmol), potassium carbonate (1.41 g, 10.2 mmol) in acetone (100 mL) was stirred at ambient temperature overnight. The mixture was cooled, filtered, and concentrated to a yellow solid. This residue was recrystallized from ethyl acetate/ether to give 1.02 g (73%) of 6-fluoro-7-benzyloxychroman-4-one in two crops as cream white crystals which had: mp 155-156° C.; NMR δ 7.58 (d, J=11 Hz, 1 H), 7.46-7.33 (m, 5 H), 6.54 (d, J=6.7 Hz, 1 H), 5.16 (d, 2 H), 4.50 (t, J=6.4 Hz, 2 H), 2.75 (t, J=6.4 Hz, 2 H). Analysis calculated for C16H13FO2 : C, 70.58; H, 4.81. Found: C, 70.45; H, 4.80.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated to a yellow solid
  4. customThis residue was recrystallized from ethyl acetate/ether

Quellen und Nachweise

ORD-Eintrag
ord-4e3bfe26b5ce41ff92bb2952fe87a9e1
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046213

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