Water → (3-Nitro-5-(trifluoromethyl)phenyl)methanol

HRID 217498

Reaktionsgleichung

Reaktionsgleichung von HRID 217498
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].B.C1COCC1.O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acidHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3-nitro-5-(trifluoromethyl)benzoic acid (2.0 g, 8.5 mmol) in THF (100 mL) was added borane-THF (17 mL of a 1 M solution in THF, 17 mmol). The reaction was stirred at 60° C. for 24 hours and then poured into H2O (50 mL). The resultant mixture was extracted with EtOAc (100 mL) and the organic layer was washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 50% EtOAc/hexanes afforded [3-nitro-5-(trifluoromethyl)phenyl]methanol. Rf=0.35 (75% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) 8.44 (s, 1H), 8.40 (s, 1H), 7.98 (s, 1H), 4.91 (s, 2H), 2.07 (bs, 1H).

Aufarbeitung

  1. extractionThe resultant mixture was extracted with EtOAc (100 mL)
  2. washthe organic layer was washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 50% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-169e8ca2fb414140b5e24eabfa5492f4
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193365B2

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