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

HRID 40274

Reaktionsgleichung

Reaktionsgleichung von HRID 40274
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([Cl:11])[CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([Cl:11])[CH:3]=1

Komponenten

3

Edukt 1

HCID 1088294-Bromo-2-chlorobenzoic acid

Produkt 1

HCID 43805739(4-Bromo-2-chlorophenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of 4-bromo-2-chlorobenzoic acid (11.1 g, 47 mmol) in THF (100 mL) at 0° C. under nitrogen was added borane-methyl sulfide complex (9.4 ml, 94 mmol) via syringe over 10 min. Gas evolution quite evident. Ice bath removed, and once gas evolution subsided reaction gently heated to reflux for 1 h. Reaction slowly quenched with MeOH (50 mL) and 2M HCl (20 mL). Aqueous extracted with 9:1 CHCl3/IPA (150 mL). Organic dried with sat NH4Cl, MgSO4, then concentrated to a colorless oil under reduced pressure. Product crystallized after 1 week sitting neat.

Aufarbeitung

  1. customIce bath removed
  2. customreaction
  3. temperaturegently heated
  4. temperatureto reflux for 1 h
  5. customReaction
  6. customslowly quenched with MeOH (50 mL) and 2M HCl (20 mL)
  7. extractionAqueous extracted with 9:1 CHCl3/IPA (150 mL)
  8. dry with materialOrganic dried with sat NH4Cl, MgSO4
  9. concentrationconcentrated to a colorless oil under reduced pressure
  10. customProduct crystallized after 1 week

Quellen und Nachweise

ORD-Eintrag
ord-a5ee826e352540d6b4248f3334706d32
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524900B2

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