1,1'-Carbonyldiimidazole → 2-Fluoro-5-(hydroxymethyl)benzonitrile

HRID 2171351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171351
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[F:12])[C:6](O)=[O:7])#[N:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[BH4-].[Na+]>O1CCCC1>[F:12][C:11]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[C:1]#[N:2]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27739323-Cyano-4-fluorobenzoic acidHCID 4311764Sodium borohydride

Produkt 1

HCID 27739342-Fluoro-5-(hydroxymethyl)benzonitrileAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-cyano-4-fluorobenzoic acid (1.00 g, 6.06 mmol) in tetrahydrofuran (THF) (20 mL) was added dropwise CDI (1.47 g, 9.08 mmol) at 0° C. After at room temperature for 30 min, sodium borohydride (0.687 g, 18.2 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 16 h, quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The organic part was separated, dried over Na2SO4, filtered and concentrated. Purification via flash column (petroleum ether/ethyl acetate=10/1) afforded the title product (350 mg).

Aufarbeitung

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. customThe organic part was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash column (petroleum ether/ethyl acetate=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-bfd939c5df034e318ddb2bc5a3360afa
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051325B2

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