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

HRID 341732ノート

反応式

HRID 341732 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 152187374-Chloro-3-fluoro-2-methylsulphenylbenzoic acid収率 69.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-06a2560bd85649169a0422b5fa4d279d
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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