Citric Acid → 3-Bromopyridine-2-carbaldehyde

HRID 509327

반응식

HRID 509327 반응식
[Br:1][C:2]1[C:3]([CH:8](Br)Br)=[N:4][CH:5]=[CH:6][CH:7]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:14]>N1CCOCC1.CCOC(C)=O>[Br:1][C:2]1[C:3]([CH:8]=[O:14])=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 311Citric AcidHCID 860725443-bromo-2-(dibromomethyl)Pyridine

생성물 1

HCID 164142313-Bromopyridine-2-carbaldehyde

시약·촉매·용매 2

HCID 8083Morpholine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A suspension of 3-bromo-2-dibromomethyl-pyridine (10.0 g, 30.32 mmole) in morpholine (30.0 mL) was heated to 60° C. for 1 h. The reaction mixture was cooled to rt and diluted with EtOAc (200 mL). The pH was adjusted to 4.0 by adding citric acid (40.0 g). The reaction mixture was then extracted with EtOAc (3×200 mL) and the combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography using silica (100-200 mesh) using 3% EtOAc in hexane as eluent to give 3-bromo-pyridine-2-carbaldehyde. 1H-NMR (400 MHz, CDCl3): c 10.23 (s, 1H), 8.74-8.76 (d, 1H), 8.02-8.04 (d, 1H), 7.26-7.38 (t, 1H).

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionThe reaction mixture was then extracted with EtOAc (3×200 mL)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-496c42a16afb4affbac7088b8bc558f5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096527B2

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