Carbon Dioxide → 2-Fluoro-6-iodo-3-methylbenzoic acid

HRID 239868

Reaktionsgleichung

Reaktionsgleichung von HRID 239868
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Li+].CC([N-]C(C)C)C.[C:18](=[O:20])=[O:19]>C1COCC1>[F:1][C:2]1[C:3]([CH3:9])=[CH:4][CH:5]=[C:6]([I:8])[C:7]=1[C:18]([OH:20])=[O:19]

Komponenten

5

Edukt 3

HCID 280Carbon DioxideHCID 1234922-Fluoro-4-iodotolueneHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 161248372-Fluoro-6-iodo-3-methylbenzoic acidAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A −78° C. solution of 2-fluoro-4-iodo-1-methylbenzene (25 g, 105.9 mmol) in THF (200 mL) was treated dropwise with LDA (2M solution in THF, 58.5 mL, 116 mmol), stirred at −78° C. for 1 hour, treated with excess powdered dry ice, stirred at −78° C. for 30 minutes, and warmed to room temperature gradually over about 18 hours. The mixture was concentrated and the residue was partitioned between 4N NaOH and diethyl ether. The aqueous phase was adjusted to pH 2 with 2N HCl and extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide 19.4 g (66% yield) of the desired product. MS (ESI(+)) m/e 279 (M+H)+.

Aufarbeitung

  1. stirringstirred at −78° C. for 30 minutes
  2. temperaturewarmed to room temperature gradually over about 18 hours
  3. concentrationThe mixture was concentrated
  4. customthe residue was partitioned between 4N NaOH and diethyl ether
  5. extractionextracted three times with ethyl acetate
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-911c3cb547b0486b839dcebae617c252
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642776B2

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