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

HRID 2261499ノート

反応式

HRID 2261499 の反応式
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

参加物

10

反応物 4

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

生成物 1

HCID 2316052-(2-methoxyphenyl)pyridine収率 95%

試薬・触媒・溶媒 5

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-444e372e5ec849beb3e64887eef7ddb7
出典データセット
uspto-grants-2010_12
特許番号
US07847039B2

反応ノート

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