2-Acetoxymethyl-5-bromopyridine → (5-Bromopyridin-2-yl)methanol

HRID 254691

Reaktionsgleichung

Reaktionsgleichung von HRID 254691
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][N:7]=1)(=O)C>Cl>[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][N:7]=1

Komponenten

3

Edukt 1

HCID 668935372-Acetoxymethyl-5-bromopyridine

Produkt 1

HCID 5200169(5-Bromopyridin-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A solution of 40 g (170 mmol) 2-(acetoxymethyl)-5-bromopyridine in conc. HCl (200 ml) was heated to reflux for 1 hour. The solution was concentrated in vacuo and the residue was neutralized with aq. KHCO3 and extracted with CH2Cl2. Concentration of the extract afforded 2-hydroxymethyl-5-bromopyridine. 1H-NMR (400 MHz, DMSO) δ 8.57 (d, J=2.4 Hz, 1H), 8.00 (m, 1H), 7.42 (q, J1=8.4 Hz, J2=0.6 Hz, 1H), 5.49 (t, J=5.4 Hz, 1H), 4.50 (d, J=4.8 Hz, 2H) m/z: 189.12 (M+1)

Aufarbeitung

  1. temperatureto reflux for 1 hour
  2. concentrationThe solution was concentrated in vacuo
  3. extractionextracted with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-d1cf1d58218046f795590130864e0c56
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875636B2

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