Sodium Iodide → 4-Iodomethyl benzoic acid tert-butyl ester

HRID 1401889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401889
[I-:1].[Na+].[C:3]([O:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][CH:10]=1)([CH3:6])([CH3:5])[CH3:4]>CC(C)=O>[C:3]([O:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][I:1])=[CH:11][CH:10]=1)([CH3:6])([CH3:5])[CH3:4]

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 18959012tert-Butyl 4-(chloromethyl)benzoate

Produkt 1

HCID 672121184-Iodomethyl benzoic acid tert-butyl esterAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Sodium iodide (229.2 g) was added to a solution of 4-chloromethyl benzoic acid tert-butyl ester (315.2 g) in acetone (1.5 L). The reaction mixture was heated to reflux for about 2 h and then allowed to cool to room temperature. The precipitate was removed by filtration and the filtrate concentrated under reduced pressure. The residue was partitioned between water (500 mL) and MTBE (1500 mL). The organic phase was washed with saturated sodium bicarbonate and dried over magnesium sulfate. Concentration under reduced pressure afforded 442.2 g (97% yield) dark oil. HNMR: CDCl3, 1.59 ppm (s, 9H), 4.47 (s, 2H), 7.42 (d, 2H), 7.91 (d, 2H)

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for about 2 h
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was partitioned between water (500 mL) and MTBE (1500 mL)
  6. washThe organic phase was washed with saturated sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-461521255155434faf7c67db3f319f13
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907103B2

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