Borane;tetrahydrofuran → (4-Bromo-3-(trifluoromethyl)phenyl)methanol

HRID 1036177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036177
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].B.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 247213904-Bromo-3-(trifluoromethyl)benzoic acid

Produkt 1

HCID 45933700(4-Bromo-3-(trifluoromethyl)phenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 4-bromo-3-(trifluoromethyl)benzoic acid 46-2 (1.35 g, 5 mmol) in THF (10 mL) was added 1M BH3.THF in THF (20 mL) slowly at 0° C. The mixture was warmed up to room temperature and stirred for 4 hours. The reaction was quenched with water at 0° C. All the solvents were evaporated and the residue was redissolved in ethyl acetate (100 mL), washed with saturated NaHCO3 aqueous solution, water and brine, dried over Na2SO4, and then concentrated. The crude product was purified by silica gel flash chromatography, eluted with 40% ethyl acetate in hexane to give (4-bromo-3-(trifluoromethyl)phenyl)methanol 46-3 as white solid. MS m/z 237.1 (M+1)

Aufarbeitung

  1. customThe reaction was quenched with water at 0° C
  2. customAll the solvents were evaporated
  3. dissolutionthe residue was redissolved in ethyl acetate (100 mL)
  4. washwashed with saturated NaHCO3 aqueous solution, water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel flash chromatography
  8. washeluted with 40% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-cda36ebcd0bc4ac6bf096f3e0593ce4b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546396B2

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