Diethyl Ether → 1-(4-Bromo-2-chlorophenyl)ethan-1-one

HRID 219169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219169
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[C:4]([Cl:14])[CH:3]=1.[CH3:15][Mg]Br.C(OCC)C>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](=[O:7])[CH3:15])=[C:4]([Cl:14])[CH:3]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 598430764-bromo-2-chloro-N-methoxy-N-methylbenzamideHCID 178418573HCID 178418573, VerbindungHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 155609501-(4-Bromo-2-chlorophenyl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of 4-bromo-2-chloro-N-methoxy-N-methylbenzamide (890 mg, 3195 μmol) in THF (10 mL) at −5° C. under nitrogen was slowly added methylmagnesium bromide 3.0 m in diethyl ether (1278 μl, 3834 μmol). After 30 min another 1.3 mL (3.8 mmol; 1.2 eq) of MeMgBr added at 23° C. After an additional hour, LCMS suggests 95% conversion. Reaction quenched with sat NH4Cl (10 mL) and resulting white cake washed repeatedly with diethyl ether. Combined organics washed with water and sat NaCl then pushed through a plug of silica (10 g). 1-(4-bromo-2-chlorophenyl)ethanone isolated as a colorless oil.

Aufarbeitung

  1. customat −5° C.
  2. waitAfter an additional hour
  3. customReaction
  4. customquenched with sat NH4Cl (10 mL)
  5. customresulting white cake
  6. washwashed repeatedly with diethyl ether
  7. washCombined organics washed with water

Quellen und Nachweise

ORD-Eintrag
ord-0e21f069e41e4751ad3c84a4942412da
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198448B2

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