Hydrochloric Acid → 1-(2-Bromo-5-chlorophenyl)ethanone

HRID 2415552

Reaktionsgleichung

Reaktionsgleichung von HRID 2415552
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:6]=1[C:7](N(OC)C)=[O:8].Cl.O>O1CCCC1.C1(C)C=CC=CC=1.O1CCCC1>[Br:4][C:5]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:6]=1[C:7](=[O:8])[CH3:1]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 222365462-Bromo-5-chloro-N-methoxy-N-methylbenzamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 124866171-(2-Bromo-5-chlorophenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 22635083Tetrahydrofuran tolueneLösungsmittel

Versuchsvorschrift

Methylmagnesium bromide (4.26 mL of a 1.4M solution in tetrahydrofuran/toluene, 5.97 mmol) was added dropwise to a stirred solution of 2-bromo-5-chloro-N-methoxy-N-methylbenzamide (3-1) (0.554 g, 1.99 mmol) in tetrahydrofuran (20 mL) at approximately 0° C. After 1 h, 1N hydrochloric acid (5 mL) was added and the resulting biphasic mixture was stirred vigorously for about 10 min. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0-10% ethyl acetate/hexanes as eluent) provided 3-3 (0.44 g) as a colorless oil.

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0-10% ethyl acetate/hexanes as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-994732bb6d2942fbb576ed31e579f72d
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06818658B2

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