Ethylene Glycol → 2-Bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine

HRID 707235

반응식

HRID 707235 반응식
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Br:10])=[N:8][CH:9]=1)(=[O:3])[CH3:2].[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:10][C:7]1[CH:6]=[CH:5][C:4]([C:1]2([CH3:2])[O:13][CH2:12][CH2:11][O:3]2)=[CH:9][N:8]=1

참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 156681955-Acetyl-2-bromopyridine

생성물 1

HCID 857750992-Bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine수율 79%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
140 °C

실험 절차

A mixture of 5-acetyl-2-bromopyridine (0.6 g, 3.00 mmol), ethylene glycol (0.535 ml, 9.60 mmol), p-toluenesulfonic acid monohydrate (0.171 g, 0.900 mmol), and toluene (12.00 ml) was stirred at 140° C. for 5 hours. The reaction mixture was washed with saturated sodium bicarbonate and brine. The aqueous layer was back extracted with ethyl acetate and the combined organics dried with magnesium sulfate and concentrated to give crude 2-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine (0.575 g, 2.356 mmol, 79% yield) as an orange oil. It was used without further purification.

후처리

  1. washThe reaction mixture was washed with saturated sodium bicarbonate and brine
  2. extractionThe aqueous layer was back extracted with ethyl acetate
  3. dry with materialthe combined organics dried with magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-709de68ecef14f7bb3f15a90f7ea0293
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

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