Benzene, 1-bromo-3,5-dimethyl- → (3,5-dimethylphenyl)(2-methylcyclopropyl)Methanone

HRID 1956544

Reaktionsgleichung

Reaktionsgleichung von HRID 1956544
Br[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([Li])CCC.CON(C)[C:18]([CH:20]1[CH2:22][CH:21]1[CH3:23])=[O:19]>CCCCCC>[CH3:9][C:4]1[CH:3]=[C:2]([C:18]([CH:20]2[CH2:22][CH:21]2[CH3:23])=[O:19])[CH:7]=[C:6]([CH3:8])[CH:5]=1

Komponenten

5

Edukt 3

HCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 45084206N-methoxy-N,2-dimethylcyclopropane-1-carboxamideHCID 178418339Butyllithium

Produkt 1

HCID 21249913(3,5-dimethylphenyl)(2-methylcyclopropyl)Methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-meta-xylene (5.7 mL in 120 mL of dry tetrahydrofuran) at -78° C. was added 30.6 mL of a 1.4M solution of n-butyllithium in hexane and the mixture stirred at low temperature. After 15 minutes, a solution of 2-methylcyclopropanecarboxylic acid N-methoxy-N-methyl-amide (5.0 g in 50 mL tetrahydrofuran) was added dropwise over 5 minutes and the mixture then allowed to warm slowly to room temperature. After 1 hour, the reaction was quenched by the addition of 20 mL 2N hydrochloric acid and 40 mL water. This was extracted with ethyl acetate washed with saturated sodium bicarbonate and brine then dried over sodium sulfate to give 6.95 g of the title compound (crude).

Aufarbeitung

  1. waitAfter 1 hour
  2. customthe reaction was quenched by the addition of 20 mL 2N hydrochloric acid and 40 mL water
  3. extractionThis was extracted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialthen dried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-2e58edfe6bab43c2a29c5f2a0d3a3f59
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780437

Verknüpfte Notizen

Wird geladen…