Carbon Dioxide → 4-Chloro-2-fluoro-3-(methylthio)benzoic acid

HRID 341742

反応式

HRID 341742 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9][CH3:10].[C:11](=[O:13])=[O:12]>CCCCCC.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]([OH:13])=[O:12])=[C:4]([F:8])[C:3]=1[S:9][CH3:10]

参加物

5

反応物 2

HCID 280Carbon DioxideHCID 53633719(2-Chloro-6-fluorophenyl)(methyl)sulfane

生成物 1

HCID 541320414-Chloro-2-fluoro-3-(methylthio)benzoic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

n-Butylithium (2.5M in hexane, 140 ml) was added to a stirred, cooled solution of crude 2-chloro-6-fluorothioanisole (60.0 g) in dry tetrahydrofuran while maintaining the temperature below -70° C. The mixture was stirred at -78° C. for 3.5 hours then poured onto solid carbon dioxide pellets. It was stirred and allowed to warm to room temperature. It was evaporated to dryness and the residue was dissolved in water and washed with ether. The aqueous layer was acidified to pH1 and extracted with ether, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with hexane and filtered to give 4-chloro-2-fluoro-3-(methylsulphenyl)benzoic acid as a white solid, m.p. 183°-185° C.

後処理

  1. temperaturewhile maintaining the temperature below -70° C
  2. stirringIt was stirred
  3. temperatureto warm to room temperature
  4. customIt was evaporated to dryness
  5. dissolutionthe residue was dissolved in water
  6. washwashed with ether
  7. extractionextracted with ether
  8. washwashed with water
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customThe filtrate was evaporated to dryness
  12. customthe residue was triturated with hexane
  13. filtrationfiltered

出典と根拠

ORDレコード
ord-34596e180732413fa4e5a6f09c5b0398
出典データセット
uspto-grants-1999_01
特許番号
US05856274

関連ノート

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