Hydrochloric Acid → 2-(4-Bromophenoxy)pyridine

HRID 40698

反応式

HRID 40698 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.Cl>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 97462-FluoropyridineHCID 24758Sodium hydride

生成物 1

HCID 232019352-(4-Bromophenoxy)pyridine収率 77.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Bromophenol (2 g, 11.5 mmol) is placed in 10 ml of anhydrous DMF under nitrogen. Sodium hydride (0.51 g, 127 mmol) is added. After stirring for 20 min at ambient temperature, 2-fluoropyridine (1.05 ml, 12.1 mmol) is added and the reaction medium is heated at 105° C. for 7 h. After hydrolysis, the pH is adjusted to 8 with a 1N aqueous solution of HCl. The reaction medium is then extracted with ethyl acetate. The organic phase is washed with a saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of ethyl acetate in heptane ranging from 0% to 30%. 2.22 g of expected 2-(4-bromo-phenoxy)pyridine are obtained,

後処理

  1. temperaturethe reaction medium is heated at 105° C. for 7 h
  2. customAfter hydrolysis
  3. extractionThe reaction medium is then extracted with ethyl acetate
  4. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe crude product obtained
  8. customis chromatographed on silica gel, elution

出典と根拠

ORDレコード
ord-55b4b911dcaf480b88a1b9de8397e19c
出典データセット
uspto-grants-2013_09
特許番号
US08530477B2

関連ノート

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