Methanol → (2,3-Difluoro-5-nitrophenyl)methanol

HRID 2277752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277752
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4](O)=[O:5].CO>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[CH2:4][OH:5]

Komponenten

5

Edukt 2

HCID 887MethanolHCID 545937902,3-Difluoro-5-nitrobenzoic acid

Produkt 1

HCID 68806779(2,3-Difluoro-5-nitrophenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirring solution of 2,3-difluoro-5-nitrobenzoic acid (Butt Park Ltd.; 9.00 g; 44.3 mmol) in THF at 0° C. was added a 1M solution of borane-tetrahydrofuran complex in THF (177.3 mL; 177.3 mmol). The mixture was allowed to react at RT overnight. Then, MeOH was cautiously added to the stirred mixture while cooling with an ice bath. The batch was diluted with ethyl acetate and washed with aqueous sodium hydroxide solution (1N) and saturated aqueous sodium chloride solution. The organic phase was dried (sodium sulfate), filtered and concentrated. The residue was purified by chromatography (hexane to hexane/ethyl acetate 1:2) to give the pure product (8.20 g; 43.4 mmol).

Aufarbeitung

  1. customto react at RT overnight
  2. temperaturewhile cooling with an ice bath
  3. washwashed with aqueous sodium hydroxide solution (1N) and saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (hexane to hexane/ethyl acetate 1:2)
  8. customto give the pure product (8.20 g; 43.4 mmol)

Quellen und Nachweise

ORD-Eintrag
ord-d0443bcf5a4149899511b21693106d11
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133171B2

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