Hydrochloric Acid → 4-Chloro-3-fluoro-2-methylsulphenylbenzoic acid

HRID 341732노트

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HRID 341732 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[F:11].[CH3:12][S:13]SC.Cl>CCCCCC.O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([S:13][CH3:12])[C:3]=1[F:11]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 12232Dimethyl DisulfideHCID 27365364-Chloro-3-fluorobenzoic acid

생성물 1

HCID 152187374-Chloro-3-fluoro-2-methylsulphenylbenzoic acid수율 69.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

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온도
-40 °C

실험 절차

n-Butylithium (2.5M in hexane, 180 ml) was added dropwise to a stirred, cooled solution of 4-chloro-3-fluorobenzoic acid (37.5 g) in tetrahydrofuran while maintaining the temperature below -40° C. The mixture was stirred at -40° C. for 3 hours. Dimethyl disulphide (60.5 g) in tetrahydrofuran was added dropwise and the mixture was stirred at -40° C. for half an hour and at room temperature overnight. Hydrochloric acid (2M) was added and the layers were separated. The aqueous layer was extracted with ether and the combined organic layers were extracted with aqueous sodium hydroxide (2M). The aqueous extract was acidified to pH1 and extracted with ether. washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with n-hexane and filtered to give 4-chloro-3-fluoro-2-(methylsulphenyl)benzoic acid (32.84 g) as a white solid m.p. 149.5°-150.50° C.

후처리

  1. temperaturewhile maintaining the temperature below -40° C
  2. stirringthe mixture was stirred at -40° C. for half an hour and at room temperature overnight
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ether
  5. extractionthe combined organic layers were extracted with aqueous sodium hydroxide (2M)
  6. extractionThe aqueous extract
  7. extractionextracted with ether
  8. washwashed with water
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. customThe filtrate was evaporated to dryness
  12. customthe residue was triturated with n-hexane
  13. filtrationfiltered

출처 및 근거

ORD 기록
ord-06a2560bd85649169a0422b5fa4d279d
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856274

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