Potassium Carbonate → 4-Bromo-2-phenylpyridine

HRID 1522694ノート

反応式

HRID 1522694 の反応式
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O>[C:9]1([C:2]2[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 8171042,4-Dibromopyridine

生成物 1

HCID 134980024-Bromo-2-phenylpyridine収率 43.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture was prepared of 2,4-dibromopyridine (10 g, 42.21 mmol), phenylboronic acid (5.1 g, 42.21 mmol), and potassium carbonate (11.7 g, 84.42 mmol) in 100 mL dimethoxyethane and 40 mL of water. Nitrogen was bubbled directly into the mixture for 30 minutes. Next, tetrakis(triphenylphosphine)palladium(0) was added (244 mg, 2.11 mmol) and the mixture was heated to reflux under nitrogen overnight. The mixture was cooled and diluted with ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, and evaporated to a residue. The residue was purified by column chromatography eluting with 0, 2, and 5% ethyl acetate/hexanes. Obtained 4.28 g of a yellow liquid (43%).

後処理

  1. customNitrogen was bubbled directly into the mixture for 30 minutes
  2. additionNext, tetrakis(triphenylphosphine)palladium(0) was added (244 mg, 2.11 mmol)
  3. temperaturethe mixture was heated
  4. temperatureto reflux under nitrogen overnight
  5. temperatureThe mixture was cooled
  6. additiondiluted with ethyl acetate and water
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with ethyl acetate
  9. washThe organic layers were washed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated to a residue
  13. customThe residue was purified by column chromatography
  14. washeluting with 0, 2, and 5% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-1d74f192ecc84d71a0ef09645c809275
出典データセット
uspto-grants-2015_07
特許番号
US09076973B2

反応ノート

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