Benzyl Bromide → 2-(Benzyloxy)-1-fluoro-4-nitrobenzene
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCCCCC.C(OCC)(=O)C>CN(C=O)C.O>[CH2:18]([O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[F:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
In a 50 mL 3-neck RBF equipped with reflux condenser, magnetic stirrer and thermo pocket were charged 2-fluoro-5-nitrophenol (2.4 g), K2CO3 (3.16 g) and dry DMF (20 mL). The reaction mixture was heated at 50° C. for 30 min. followed by addition of benzyl bromide (2.87 g) in DMF and the reaction mixture was heated to 80° C. for 18 hr. The reaction was monitored on TLC using hexane:ethyl acetate (5:5) as mobile phase. The reaction was complete after 30 minutes. After completion, the reaction mixture was poured into cold water. The solid precipitate was filtered and washed with water and dried under reduced pressure at 45° C. to give 3.20 g of 2-(benzyloxy)-1-fluoro-4-nitrobenzene. 1H NMR: DMSO-d6 (400 MHz): 5.35 (s, 2H), 7.358-7.397 (m, 1H), 7.415-7.454 (m, 2H), 7.448-7.530 (m, 2H), 7.553-7.579 (m, 1H), 7.900-7.939 (m, 1H), 8.091-8.116 (dd, 1H, J=2.8, 4.4).
Aufarbeitung
- customIn a 50 mL 3-neck RBF equipped
- temperaturewith reflux condenser, magnetic stirrer
- temperaturethe reaction mixture was heated to 80° C. for 18 hr
- filtrationThe solid precipitate was filtered
- washwashed with water
- customdried under reduced pressure at 45° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-66bcb0e65d6f43b9869941c81b95a463
- Quelldatensatz
- uspto-grants-2016_08
- Patentnummer
- US09415049B2
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