Water → Benzene, 1-bromo-3-fluoro-4-(methylthio)-2-(trifluoromethyl)-

HRID 341736

반응식

HRID 341736 반응식
N([O-])=O.[Na+].[Br:5][C:6]1[CH:12]=[CH:11][C:9](N)=[C:8]([F:13])[C:7]=1[C:14]([F:17])([F:16])[F:15].[CH3:18][S:19]SC.O>S(=O)(=O)(O)O.C(O)(=O)C.[Cu]>[Br:5][C:6]1[C:7]([C:14]([F:17])([F:16])[F:15])=[C:8]([F:13])[C:9]([S:19][CH3:18])=[CH:11][CH:12]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 12232Dimethyl DisulfideHCID 23668193Sodium NitriteHCID 536697144-Bromo-2-fluoro-3-(trifluoromethyl)aniline

생성물 1

HCID 53772445Benzene, 1-bromo-3-fluoro-4-(methylthio)-2-(trifluoromethyl)-

시약·촉매·용매 3

HCID 23978Copper촉매HCID 176Acetic Acid용매2회HCID 1118Sulfuric Acid용매

반응 조건

온도
5 °C

실험 절차

A solution of sodium nitrite (11.2 g) in concentrated sulphuric acid was added to a stirred cooled suspension of 4-bromo-2-fluoro-3-trifluoromethylaniline (40 g) in glacial acetic acid while maintaining the temperature below 5° C. The mixture was stirred at 5° C. for one and a half hours. The resultant mixture was added gradually to a mixture of dimethyl disulphide (20 ml) and copper power (0.224 g) in glacial acetic acid at 45° C. It was stirred and heated at 70° C. for 3 hours. It was cooled, poured into water, extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and purified by column chromatography eluted with petroleum spirit (b.p. 60°-80° C.) to give 6-bromo-2-fluoro-3-(methylsulphenyl)benzotrifluoride (30.6 g) as an orange oil NMR (CDCl3) 2.45(s,3H), 7.25(t,1H), 7.5(d,1H).

후처리

  1. temperaturecooled
  2. temperaturewhile maintaining the temperature below 5° C
  3. stirringIt was stirred
  4. temperatureheated at 70° C. for 3 hours
  5. temperatureIt was cooled
  6. extractionextracted with ether
  7. washwashed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. custompurified by column chromatography
  12. washeluted with petroleum spirit (b.p. 60°-80° C.)

출처 및 근거

ORD 기록
ord-53ab50e7bcd246aa8df902be426b2b2b
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856274

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