Benzyl Bromide → 2-(Benzyloxy)-1-chloro-4-nitrobenzene

HRID 37832

Reaktionsgleichung

Reaktionsgleichung von HRID 37832
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[OH:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:19][C:11]1[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=1[Cl:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 692642-Chloro-5-nitrophenol

Produkt 1

HCID 128819332-(Benzyloxy)-1-chloro-4-nitrobenzeneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Benzyl bromide (0.6 mL, 5.04 mmol) was added dropwise to a mixture of 2-chloro-5-nitro-phenol (800 mg, 4.61 mmol) and potassium carbonate (1.27 g, 9.22 mmol) in acetone (20 mL) at room temperature and heated at reflux for 2 h. Inorganic salts were filtered off and washed with acetone (20 mL). The combined filtrate and washings were concentrated in vacuo, the resulting residue then being dissolved in ethyl acetate (25 mL) and washed successively with water (2×20 mL), brine (20 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to yield 2-benzyloxy-1-chloro-4-nitro-benzene (1.20 g, 99%) as a cream solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. filtrationInorganic salts were filtered off
  4. washwashed with acetone (20 mL)
  5. concentrationThe combined filtrate and washings were concentrated in vacuo
  6. dissolutionthe resulting residue then being dissolved in ethyl acetate (25 mL)
  7. washwashed successively with water (2×20 mL), brine (20 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c6b6cd300ebe4d5bb2b195e5a8862289
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524705B2

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