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

HRID 648710

반응식

HRID 648710 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1f25bb1b3f7d4601ac0e3d68f9532471
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04736037

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