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

HRID 341736ノート

反応式

HRID 341736 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 176Acetic Acid溶媒2 回HCID 1118Sulfuric Acid溶媒

反応条件

温度
5 °C

実験手順

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).

後処理

  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.)

出典と根拠

ORDレコード
ord-53ab50e7bcd246aa8df902be426b2b2b
出典データセット
uspto-grants-1999_01
特許番号
US05856274

反応ノート

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