2-Bromo-4-chlorobenzoic acid → (2-Bromo-4-chlorophenyl)methanol

HRID 252114

Reaktionsgleichung

Reaktionsgleichung von HRID 252114
B.C1COCC1.[Br:7][C:8]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11]>C1COCC1>[Br:7][C:8]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:9]=1[CH2:10][OH:11]

Komponenten

4

Edukt 2

HCID 331262-Bromo-4-chlorobenzoic acidHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 54049764(2-Bromo-4-chlorophenyl)methanolAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add borane-THF (1 M in THF, 3.2 mL) complex dropwise to an ice-cooled solution of 2-bromo-4-chlorobenzoic acid (500 mg, 2.1 mmol) in THF (2 mL). Remove the cooling bath and stir overnight. Slowly add water (1 mL) and solid sodium carbonate. Stir 1 h. Filter and wash solids with THF. Chromatograph on silica gel, eluting with 0:100 to 30:70 ethyl acetate:dichloromethane to give 2-bromo-4-chlorobenzyl alcohol as a white solid (378 mg, 80%).

Aufarbeitung

  1. customRemove the cooling bath
  2. stirringStir 1 h
  3. filtrationFilter
  4. washwash solids with THF
  5. washChromatograph on silica gel, eluting with 0:100 to 30:70 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-99fc7593d3714863940340fb8582927e
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868014B2

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