Carbon Dioxide → Benzoic acid, 2-(methylthio)-4-(trifluoromethyl)-

HRID 21461

反応式

HRID 21461 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[S:17][CH3:18].[C:19](=[O:21])=[O:20].Cl>CCOCC>[CH3:18][S:17][C:8]1[CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=[CH:12][C:7]=1[C:19]([OH:21])=[O:20]

参加物

6

反応物 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 11000144Benzene, 1-bromo-2-(methylthio)-4-(trifluoromethyl)-HCID 178418339Butyllithium

生成物 1

HCID 11085762Benzoic acid, 2-(methylthio)-4-(trifluoromethyl)-

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

n-Butyllithium (2.5M in hexane, 25 ml) was added under an inert atmosphere to a stirred solution of 4-bromo-3-(methylsulphenyl)benzotrifluoride (16.4 g) in ether maintaining the temperature below -70° C. for 2 hours. The mixture was poured onto solid carbon dioxide pellets, stirred for 10 rains and aqueous hydrochloric acid added. The layers were separated and the aqueous layer was extracted with ether. The combined organic layers were washed with water, dried (MgSO4) and filtered. The filtrate was evaporated and the residue was triturated with cyclohexane and filtered to give 2-(methylsulphenyl)-4-trifluoromethylbenzoic acid (12.4 g) as a white solid NMR (CDCl3 +DMSO-d6): 2.45 (s,3H), 7.2(d,1H), 7.3(s,1H), 8.0(d,1H), 10.7-11(bs,1H).

後処理

  1. additionadded
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ether
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customthe residue was triturated with cyclohexane
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-4b763ab9c11f46fdbe59706e9ea487f7
出典データセット
uspto-grants-1995_06
特許番号
US05424276

関連ノート

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