2-Bromopyridine → 2-(2-methoxyphenyl)pyridine

HRID 2261499노트

반응식

HRID 2261499 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)C.C(COC)OC.O>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

10

반응물 4

HCID 79732-BromopyridineHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 27339582-Methoxyphenylboronic acid

생성물 1

HCID 2316052-(2-methoxyphenyl)pyridine수율 95%

시약·촉매·용매 5

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 80711,2-Dimethoxyethane용매

실험 절차

2-Bromopyridine (4.28 mL, 43.9 mmol), 2-methoxyphenylboronic acid (6.7 g, 43.9 mmol), palladium acetate (0.14 g, 0.62 mmol), triphenylphosphine (0.6 mg, 2.3 mmol) and potassium phosphate (9.40 g, 44.3 mmol) were added to a flask. A mixture solution of 10 mL of water and 40 mL of dimethoxyethane was added and reflux was performed for 6 hours. After cooling to room temperature, aqueous ammonium chloride solution (50 mL) and diethyl ether (100 mL) were added. The organic layer was separated. After extracting the residue using diethyl ether, the collected organic layer was dried with magnesium sulfate. After removing volatile materials, followed by purification via silica gel chromatography using n-hexane, 7.7 g (yield: 95%) of 2-(2′-methoxyphenyl)pyridine was obtained as colorless liquid.

후처리

  1. temperaturereflux
  2. customThe organic layer was separated
  3. extractionAfter extracting the residue
  4. dry with materialthe collected organic layer was dried with magnesium sulfate
  5. customAfter removing volatile materials
  6. customfollowed by purification via silica gel chromatography

출처 및 근거

ORD 기록
ord-444e372e5ec849beb3e64887eef7ddb7
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07847039B2

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