Potassium Carbonate → 4-Chloro-2-[(4-fluorophenyl)sulfanyl]benzoic acid

HRID 2083765노트

반응식

HRID 2083765 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.I[C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[Cl:19][C:17]1[CH:18]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[C:15]([S:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:16]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 677894-FluorothiophenolHCID 1394524-Chloro-2-iodobenzoic acid

생성물 1

HCID 203575284-Chloro-2-[(4-fluorophenyl)sulfanyl]benzoic acid

시약·촉매·용매 1

HCID 1049Pyridine용매2회

실험 절차

To a solution of 1.28 g. (0.01 mol) of p-fluorothiophenol and 2.82 g. (0.01 mol) of 2-iodo-4-chlorobenzoic acid in 20 ml. of pyridine is added 1.3 g. (0.01 mol) of potassium carbonate, with stirring. Additional pyridine is added until solution is clear and then 0.3 g. of cuprous chloride is introduced. The resulting mixture is refluxed overnight, poured into ice-water, stirred and filtered. The aqueous solution is acidified and filtered. The solid is dissolved in 5% sodium bicarbonate solution and this solution is extracted with ether. The aqueous solution is acidified, extracted with ether and the washed, dried extract is concentrated to give 4-chloro-2-(4-fluorophenylthio)-benzoic acid, m.p. 204°-213° C. The latter (6.5 g., 0.023 mol) is heated for one hour with 105 g. of sulfuric acid to obtain 2-fluoro-6-chloro-9-thioxanthone, m.p 222°-224° C.

후처리

  1. temperatureThe resulting mixture is refluxed overnight
  2. filtrationfiltered
  3. filtrationfiltered
  4. dissolutionThe solid is dissolved in 5% sodium bicarbonate solution
  5. extractionthis solution is extracted with ether
  6. extractionextracted with ether
  7. customthe washed, dried
  8. extractionextract
  9. concentrationis concentrated

출처 및 근거

ORD 기록
ord-1e16c3fbc57646059c1e94689ed9a037
출처 데이터셋
uspto-grants-1978_04
특허 번호
US04086350

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