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

HRID 1491586ノート

反応式

HRID 1491586 の反応式
C([Li])CCC.[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[F:16].[CH3:17][S:18]SC.Cl>O1CCCC1>[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([S:18][CH3:17])[C:8]=1[F:16]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 12232Dimethyl DisulfideHCID 27365364-Chloro-3-fluorobenzoic acidHCID 178418339Butyllithium

生成物 1

HCID 152187374-Chloro-3-fluoro-2-methylsulphenylbenzoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Butyllithium (2.5M in hexane; 180 ml) was added dropwise with stirring to a cooled solution of 4-chloro-3-fluorobenzoic acid (37.5 g) in tetrahydrofuran at -40° C. for 3 hours. A solution of dimethyldisulphide (60.5 g) in tetrahydrofuran was added and the mixture was stirred 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 solution (2M). The aqueous layer was acidified to pill and extracted with ether, washed with water, dried (sodium sulphate) and filtered. The flitrate 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 8) as a yellow solid m.p. 149.5°-150.5° C.

後処理

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with ether
  3. extractionthe combined organic layers were extracted with aqueous sodium hydroxide solution (2M)
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried (sodium sulphate)
  7. filtrationfiltered
  8. customThe flitrate was evaporated to dryness
  9. customthe residue was triturated with n-hexane
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-6c802ce3151144d98f8c7036791f8f43
出典データセット
uspto-grants-1994_12
特許番号
US05371064

反応ノート

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