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m-Tolylacetic acid → 2-(3-(Bromomethyl)phenyl)acetic acid

HRID 990908
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 990908
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:12][CH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 12121m-Tolylacetic acidHCID 67184N-bromobutanimide

Produkt 1

HCID 103765092-(3-(Bromomethyl)phenyl)acetic acidAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of 3-methylphenylacetic acid (125 g) in tetrachloro methane (1660 ml), N-bromosuccinimide (148 g) and 2,2′-azobisisobutyronitrile (AIBN; 1.37 g) were added. The mixture was refluxed with heating. After termination of reaction, the solution was cooled with ice. The white precipitate was filtered by glass-filter. The filtrate was washed by tetrachloro methane. The filtrate together with washing liquid was concentrated. The obtained residue was dissolved into ethyl acetate. Thereto, hexane was added. The mixture was crystallized to obtain the title compound (59 g).

Aufarbeitung

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating
  3. customAfter termination of reaction
  4. temperaturethe solution was cooled with ice
  5. filtrationThe white precipitate was filtered
  6. filtrationby glass-filter
  7. washThe filtrate was washed by tetrachloro methane
  8. washThe filtrate together with washing liquid
  9. concentrationwas concentrated
  10. dissolutionThe obtained residue was dissolved into ethyl acetate
  11. additionThereto, hexane was added
  12. customThe mixture was crystallized

Quellen und Nachweise

ORD-Eintrag
ord-48e55850629f48fba4cc1d5c56cfd73b
Quelldatensatz
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06462081B1

Notizen zur Reaktion

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