Methanol → (2-Chloro-5-fluorophenyl)methanol

HRID 240286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 240286
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[C:4](OC)=[O:5].[BH4-].[Na+].CO.O>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:3]=1[CH2:4][OH:5]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 23331706Methyl 2-chloro-5-fluorobenzoate

Produkt 1

HCID 2773605(2-Chloro-5-fluorophenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-chloro-5-fluorobenzoate (23, 35.0 g, 185.6 mmol) in dry THF (150 mL) was added NaBH4 (21.2 g, 557 mmol). Methanol (40 mL) was added dropwise at RT. After the addition, the mixture was stirred at RT for 1 h. Water (300 mL) was slowly added. The mixture was extracted with CH2Cl2 (200 mL×2). The combined extracts were washed with saturated NaHCO3 and brine, dried over MgSO4, and concentrated to give (2-chloro-5-fluorophenyl)methanol (24).

Aufarbeitung

  1. additionAfter the addition
  2. extractionThe mixture was extracted with CH2Cl2 (200 mL×2)
  3. washThe combined extracts were washed with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-be01f19b82354f439dee987c8818fd9f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648073B2

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