Hydrochloric Acid → 2-(4-Methoxyphenyl)pyridine

HRID 747081노트

반응식

HRID 747081 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.BrC1C=CC(OC)=CC=1.[Mg].Br[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:5][CH:4]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 77304-BromoanisoleHCID 79732-BromopyridineHCID 5462224MagnesiumHCID 178491912HCID 178491912, 화합물

생성물 1

HCID 2202392-(4-Methoxyphenyl)pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

That is, as shown in the Reaction Scheme below, (4-methoxyphenyl)magnesium bromide was synthesized from 22.4 g (120 mmol) of 4-bromoanisole by a conventional method by using 3.4 g of magnesium (Mg) in dry tetra hydrofuran (THF) under argon stream and added slowly into a solution of 15.8 g (100 mmol) of 2-bromopyridine and 1.8 g of (1,2-bis(diphenylphosphino)-ethane)dichloronickel (II) (Ni(dppe)Cl2) in dry THF and the mixture was refluxed for 1 hour. After adding 250 ml of an aqueous solution of 5% hydrochloric acid to the reaction mixture, the reaction mixture was washed with chloroform. The water layer was neutralized with an aqueous solution of sodium hydrogen carbonate and the objective compound was extracted with chloroform and the organic layer was distilled off under reduced pressure. The distillate immediately solidified at room temperature to obtain 15.1 g (81.5 mmol) of 2-(4-methoxy-phenyl)pyridine (4-MeO—PPy) as white solid. Identification was performed by elementary analysis of C, H and N and 1H-NMR.

후처리

  1. temperaturethe mixture was refluxed for 1 hour
  2. washthe reaction mixture was washed with chloroform
  3. extractionthe objective compound was extracted with chloroform
  4. distillationthe organic layer was distilled off under reduced pressure
  5. customimmediately solidified at room temperature

출처 및 근거

ORD 기록
ord-6bf36499ad7e4e82af3353b017546e8d
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396598B2

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