Benzyl Bromide → 4-Benzyloxymethyl-2-methoxy-1-nitro-benzene

HRID 1821792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821792
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH2:12][OH:13].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)C>[CH2:20]([O:13][CH2:12][C:11]1[CH:14]=[CH:15][C:16]([N+:17]([O-:19])=[O:18])=[C:9]([O:8][CH3:7])[CH:10]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 6029613-Methoxy-4-nitrobenzyl alcohol

Produkt 1

HCID 220463764-Benzyloxymethyl-2-methoxy-1-nitro-benzeneAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirred suspension of finely powdered cesium carbonate (8.0 g, 24.5 mmol) was added 3-methoxy-4-nitrobenzyl alcohol (1.5 g, 8.18 mmol), followed by benzyl bromide, (2 mL, 16.4 mmol). After stirring at room temperature for 18 h, the suspension diluted with 100 mL diethyl ether, and washed with 3×50 mL water, then 50 mL brine. The organic phase was dried over MgSO4, filtered through a plug of silica, and concentrated. The resulting orange oil was purified by flash chromatography, eluting with 2:1 hexane-EtOAc, to give 1.87 g, (84%) of the benzyl ether. 1H NMR (400 MHz, CDCl3): δ 7.85 (d, J=8.2 Hz, 1H) 7.3-7.4 (m, 5H), 7.26 (s, 1H), 6.97 (d, J=8.2 Hz, 1H), 4.61 (s, 2H), 4.59 (s, 2H), 3.96 (s, 3H).

Aufarbeitung

  1. washwashed with 3×50 mL water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered through a plug of silica
  4. concentrationconcentrated
  5. customThe resulting orange oil was purified by flash chromatography
  6. washeluting with 2:1 hexane-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-5b9bd45166a2418e9362118064465109
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608618B2

Notizen zur Reaktion

Wird geladen…