Methanol → 2-(3,5-difluorophenyl)-2-methoxyacetic acid

HRID 413866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413866
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:6].[CH:11](Br)(Br)Br.[OH-:15].[K+].[CH3:17][OH:18]>O.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]([O:6][CH3:11])[C:17]([OH:18])=[O:15])[CH:7]=[C:8]([F:10])[CH:9]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 5558BromoformHCID 14797Potassium HydroxideHCID 5881603,5-Difluorobenzaldehyde

Produkt 1

HCID 223929272-(3,5-difluorophenyl)-2-methoxyacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

The title compound was prepared according to the general procedure in Reeve, et al, J.A.C.S., 83 :2755 (1961). A solution of 3,5-difluorobenzaldehyde (Aldrich) and bromoform (1.2 eq.) In methanol was cooled to −5° C. and treated dropwise with methanolic KOH. The reaction temperature was held below 6 C during the addition. The mixture was slowly warmed to room temperature and stirred overnight. The suspension was diluted with water and 50% saturated aqueous brine. The mixture was extracted with ether, and the aqueous layer was acidified to a pH around 3.5 and extracted with ether. The latter organic phase was dried over sodium sulfate, filtered and concentrated. The crude acid was purified via flash chromatography eluting with 1:4:95 acetic acid/methanol/methylene chloride to give a white solid. 1H NMR (300 MHz, CDCl3) δ 11.36 (1H, bs), 7.05 (1H, m), 6.81 (2H, tt, J=2.4, 8.8 Hz), 4.77 (1H, s), 3.47 (3H, s)/C9H8F2O3 (MW=202.17); mass spectroscopy—202.

Aufarbeitung

  1. additionThe reaction temperature was held below 6 C during the addition
  2. extractionThe mixture was extracted with ether
  3. extractionextracted with ether
  4. dry with materialThe latter organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude acid was purified via flash chromatography
  8. washeluting with 1:4:95 acetic acid/methanol/methylene chloride
  9. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-549634ceea6d43b793b74dfc852e6d94
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06569851B1

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