Acetic Acid → 4-Bromo-3,5-difluorobenzonitrile

HRID 1086396노트

반응식

HRID 1086396 반응식
N([O-])=O.[Na+].S(=O)(=O)(O)O.C(O)(=O)C.[C:14]([C:16]1[CH:22]=[C:21]([F:23])[C:19](N)=[C:18]([F:24])[CH:17]=1)#[N:15].[BrH:25]>[Cu]Br.O>[Br:25][C:19]1[C:21]([F:23])=[CH:22][C:16]([C:14]#[N:15])=[CH:17][C:18]=1[F:24]

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 2804674-Amino-3,5-difluorobenzonitrileHCID 23668193Sodium Nitrite

생성물 1

HCID 147942904-Bromo-3,5-difluorobenzonitrile

시약·촉매·용매 2

HCID 24593copper(I) bromide촉매HCID 962Water용매

실험 절차

24 g of sodium nitrite was added to 180 ml of concentrated sulfuric acid cooled to a temperature of at least 10° C. 38 ml of acetic acid was added to the mixture. 53 g of 4-cyano-2,6difluoroaniline was added gradually to keep the temperature of the solution between about 20°and 25° C. The mixture was stirred at 20°-25° C. for one hour. A solution was prepared by dissolving 60 g of copper (I) bromide in 180 ml of an aqueous 48% solution of hydrobromic acid. The mixture was added drop-wise to the solution and the solution was stirred at room temperature for 15 hours. Water was added to the solution, and the solution was extracted with chloroform and washed with water. The chloroform in the aqueous layer was distilled off and the residue was recrystallized from a solution mixture of methanol and acetone, to yield 25 g of 2-bromo-5-cyano-1,3-difluorobenzene.

후처리

  1. temperaturecooled to a temperature of at least 10° C
  2. custombetween about 20°and 25° C
  3. customA solution was prepared
  4. additionThe mixture was added drop-wise to the solution
  5. stirringthe solution was stirred at room temperature for 15 hours
  6. extractionthe solution was extracted with chloroform
  7. washwashed with water
  8. distillationThe chloroform in the aqueous layer was distilled off
  9. customthe residue was recrystallized from a solution mixture of methanol and acetone

출처 및 근거

ORD 기록
ord-89731dcb29fb4002832743abd203fab7
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05030382

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