Dimethylformamide → 2-Bromo-4-methylbenzamide

HRID 657317

Reaktionsgleichung

Reaktionsgleichung von HRID 657317
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C[N:13](C=O)C>C1(C)C=CC=CC=1.S(Cl)(Cl)=O>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:13])=[O:5]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 2262922-Bromo-4-methylbenzoic acid

Produkt 1

HCID 2623402-Bromo-4-methylbenzamideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a suspension of 2-bromo-4-methylbenzoic acid (15.0 g, 69.8 mmol) in toluene (60 mL), thionyl chloride (10.3 mL) and DMF (0.10 mL) were added and stirred at 50° C. for 3 h. After cooling to room temperature, the excess thionyl chloride was removed in vacuo. The residue was dissolved in toluene (50 mL), and the mixture was added to the solution of ammonia (25%, 60 mL). The white precipitate was filtered over Celite and dried in vacuo to afford 2-bromo-4-methylbenzamide (14.8 g, 99%).

Aufarbeitung

  1. additionwere added
  2. temperatureAfter cooling to room temperature
  3. customthe excess thionyl chloride was removed in vacuo
  4. dissolutionThe residue was dissolved in toluene (50 mL)
  5. additionthe mixture was added to the solution of ammonia (25%, 60 mL)
  6. filtrationThe white precipitate was filtered over Celite
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-46a2cb238e6d4baca3a6f85a64244329
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071588B2

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