Potassium Carbonate → [4-Chloro-2-(cyclopropylmethoxy)phenyl]methanol

HRID 514456

Reaktionsgleichung

Reaktionsgleichung von HRID 514456
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([OH:8])[CH:7]=1.Br[CH:12]([CH:14]1[CH2:16][CH2:15]1)O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:9][OH:10])=[C:6]([O:8][CH2:12][CH:14]2[CH2:16][CH2:15]2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 3271485-Chloro-2-(hydroxymethyl)phenolHCID 53647370HCID 53647370, Verbindung

Produkt 1

HCID 86725580[4-Chloro-2-(cyclopropylmethoxy)phenyl]methanolAusbeute 13,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Charged 5-chloro-2-(hydroxymethyl)phenol (616 mg, 3.88 mmol, PREPARATION 7), bromocyclopropylmethanol (525 mg, 3.88 mmol), K2CO3 (1.07 g, 7.77 mmol) and DMF (6 mL) to a flask, purged with nitrogen and heated to 80° C. overnight. Poured into ice water, and extracted with ethyl acetate twice, and washed the organic phase with water twice, brine and dried with anhydrous Na2SO4, removed the solvent for silica gel chromatograph to give 108 mg of the title compound (13%). 1H NMR (400 MHz, CDCl3): δ 0.33-0.37 (2H, m), 0.63-0.68 (2H, m), 1.26-1.28 (1H, m), 3.84 (2H, d, J=7.2 Hz), 4.67 (2H, s), 4.86 (1H, s), 6.84 (1H, d, J=1.2 Hz), 6.91 (1H, dd, J=2.0 Hz, 8.0 Hz), 7.19 (1H, d, J=7.6 Hz).

Aufarbeitung

  1. custompurged with nitrogen
  2. additionPoured into ice water
  3. extractionextracted with ethyl acetate twice
  4. washwashed the organic phase with water twice
  5. dry with materialbrine and dried with anhydrous Na2SO4
  6. customremoved the solvent for silica gel chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-3e0df4d096ce4d8c87798068740605b8
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09107916B2

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