Water → Methyl 2-(6-bromopyrid-2-yloxymethyl)phenylacetate

HRID 850157

Reaktionsgleichung

Reaktionsgleichung von HRID 850157
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[OH-].[Na+].Cl[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([O:22][CH3:23])=[O:21].O>C1OCCOCCOCCOCCOC1.C1(C)C=CC=CC=1.CN(C=O)C.[I-].[Na+]>[Br:8][C:4]1[N:3]=[C:2]([O:1][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:7]=[CH:6][CH:5]=1

Komponenten

9

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 9855748Methyl 2-[2-(chloromethyl)phenyl]acetateHCID 178515930HCID 178515930, Verbindung

Produkt 1

HCID 19366333Methyl 2-(6-bromopyrid-2-yloxymethyl)phenylacetateAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 5238Sodium IodideKatalysatorHCID 3633615-Crown-5KatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxy-6-bromopyridine (1.3 g, 7.5 mmol), sodium hydroxide (0.36 g, 9.0 mmol) and 15-crown-5 (1 drop) in dry toluene (20 ml) were stirred at reflux for 1.5 hours. The toluene was removed under reduced pressure and the white salt residue was dissolved in dry DMF (10 ml). Methyl 2-chloromethylphenylacetate (1.0 g, 5 mmol) in dry DMF (10 ml) was added dropwise along with sodium iodide (10 mg). The mixture was stirred at 80° C. for 2 hours, poured into water and extracted with diethyl ether. The ether extracts were washed with water, dried and the ether removed in vacuo leaving an orange oil which was purified by column chromatography (silica eluted with 10% ethyl acetate in hexane) to give methyl 2-(6-bromopyrid-2-yloxymethyl)phenylacetate (0.86 g, 51%) (Compound No. 2 in Table 1) as an orange oil; 1H NMR (270 MHz)δ: 3.68(3H,s), 3.73(2H,s), 5.38(2H,s), 6.68(1H,d), 7.06(1H,d), 7.25-7.50(5H,m) ppm.

Aufarbeitung

  1. temperatureat reflux for 1.5 hours
  2. customThe toluene was removed under reduced pressure
  3. dissolutionthe white salt residue was dissolved in dry DMF (10 ml)
  4. stirringThe mixture was stirred at 80° C. for 2 hours
  5. extractionextracted with diethyl ether
  6. washThe ether extracts were washed with water
  7. customdried
  8. customthe ether removed in vacuo
  9. customleaving an orange oil which
  10. customwas purified by column chromatography (silica eluted with 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2d2c758f19d640058b0f3b90bd5eaee6
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06015905

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