Hydrochloric Acid → 3-Pyridinemethanol, 2-bromo-alpha-(2-chlorophenyl)-

HRID 2251954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251954
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20].Cl>C1COCC1>[Br:9][C:10]1[C:15]([CH:19]([C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[Cl:16])[OH:20])=[CH:14][CH:13]=[CH:12][N:11]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 69962-ChlorobenzaldehydeHCID 79732-BromopyridineHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 866012413-Pyridinemethanol, 2-bromo-alpha-(2-chlorophenyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Add LDA (400 mL, 0.8 mol) to 2-bromopyridine (105 g, 0.667 mol) in THF (3.2 L) at −78° C. and stir. After 2 hours, add 2-chlorobenzaldehyde (103 g, 0.733 mol) in THF (300 mL) and allow the reaction mixture to gradually warm to ambient temperature. Treat the reaction mixture with 1 M HCl (1.7 L) and extract with diethyl ether. Combine the organic layers and wash with water and brine. Dry over sodium sulfate, filter, and concentrate under reduced pressure. Purification by flash chromatography, eluting with hexane:ethyl acetate (10:1 to 1:1) gives the title compound: 1H NMR (300 MHz, CDCl3), δ8.28(dd, 1H, J=1.83, 4.73), 7.67 (dd, 1H, J=1.83, 7.63), 7.48-7.19 (m, 5H), 6.41 (s, 1H), 3.10 (bs, 1H); MS (IS) m/z 298.0 (M+1), 300.0 (M+1); Analysis for C12H9BrClNO: calcd: C, 48.27; H, 3.04; N, 4.69; found: C, 49.06; H, 3.18; N, 4.64. Rf=0.29 heptane: ethyl acetate, 2:1).

Aufarbeitung

  1. extractionextract with diethyl ether
  2. washwash with water and brine
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customPurification by flash chromatography
  7. washeluting with hexane:ethyl acetate (10:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-a9949d77e28042d4a6cc230155e38c81
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07320994B2

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