Benzyl Bromide → 1-(Benzyloxy)-3-bromo-5-nitrobenzene

HRID 712146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712146
[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([Br:1])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 104889843-Bromo-5-nitrophenol

Produkt 1

HCID 147841491-(Benzyloxy)-3-bromo-5-nitrobenzeneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-5-nitro-phenol (770 g, 3.53 mol) in acetone (10 L) was added pulverized K2CO3 (2.45 kg, 17.75 mol) in one portion at rt followed by addition of benzyl bromide (632 mL, 5.32 mol) over a period of 30 min. The resulting reaction mixture was stirred for 15 min then heated at reflux for 3 h. After reaction completion (by TLC), the reaction mixture was filtered through celite and the acetone distilled off. The crude residue thus obtained was purified over silica gel (60-120 M) using EtOAc:hexane (5:95) to obtain the desired product (551 g, 51%).

Aufarbeitung

  1. customat rt
  2. customThe resulting reaction mixture
  3. temperaturethen heated
  4. temperatureat reflux for 3 h
  5. customAfter reaction completion (by TLC)
  6. filtrationthe reaction mixture was filtered through celite
  7. distillationthe acetone distilled off
  8. customThe crude residue thus obtained
  9. customwas purified over silica gel (60-120 M)

Quellen und Nachweise

ORD-Eintrag
ord-c3c5112d04e34992a02df5f456b13ae7
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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