Fluorobenzene → 2-Chloro-4-(4-fluorobenzoyl)-pyridine

HRID 65525

反応式

HRID 65525 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5](Cl)=[O:6].[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Al+3].[Cl-].[Cl-].[Cl-].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)[CH:8]=[CH:9][N:10]=1

参加物

6

反応物 4

HCID 10008FluorobenzeneHCID 14798Sodium HydroxideHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 201457102-Chloro-4-(4-fluorobenzoyl)-pyridine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 4.2 g 2-chloro-isonicotinoyl chloride in 25 ml. fluorobenzene there is added with cooling 11.7 g AlCl3. The mixture is heated at 70°-80° C. during 7 hrs. The crude is added to acidic (pH 1-2) cold water. The pH is raised until 4.5 with diluted aqueous NaOH. This aqueous organic mixture is extracted several times with methylene chloride. The combined extracts are washed with water, dried (Na2SO4) and distilled in a rotary evaporator. The remaining crude oil is purified through a silica column, eluting with ethyl ether: petroleum ether 1:3. Yield 5 g of the title product, m.p. 60°-3° C. (cyclohexane); UV (ethanol) λmax.: 262 nm, ε=10,250; Cl 15.30 (15.05); F 8.15 (8.06).

後処理

  1. temperatureThe mixture is heated at 70°-80° C. during 7 hrs
  2. extractionThis aqueous organic mixture is extracted several times with methylene chloride
  3. washThe combined extracts are washed with water
  4. dry with materialdried (Na2SO4)
  5. distillationdistilled in a rotary evaporator
  6. customThe remaining crude oil is purified through a silica column
  7. washeluting with ethyl ether: petroleum ether 1:3

出典と根拠

ORDレコード
ord-fb11e132fb8a4f8c9668830b3e593a9f
出典データセット
uspto-grants-1986_09
特許番号
US04614833

関連ノート

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