Potassium Iodide → 2-Chloro-4-iodo-1-trifluoromethylbenzene

HRID 1096193

反応式

HRID 1096193 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10])N.C1(C)C=CC(S(O)(=O)=O)=CC=1.[I-:24].[K+].N([O-])=O.[Na+].C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC#N.O>[Cl:1][C:2]1[CH:3]=[C:4]([I:24])[CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10]

参加物

9

反応物 6

HCID 4875Potassium IodideHCID 6101p-Toluenesulfonic acidHCID 24477Sodium ThiosulfateHCID 679623-Chloro-4-(trifluoromethyl)anilineHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

生成物 1

HCID 667832122-Chloro-4-iodo-1-trifluoromethylbenzene収率 73.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 3-chloro-4-(trifluoromethyl)aniline (450 mg, 2.30 mmol) and toluene 4-sulfonic acid (1.19 g, 6.92 mmol) in CH3CN (10 mL) was added a solution of potassium iodide (955 mg, 5.76 mmol) and sodium nitrite (318 mg, 4.61 mmol) in water (1.8 mL) over 15 min at 10° C., then after 20 min the reaction mixture was poured onto water, neutralized with sat. aq. NaHCO3 solution, treated with 2 M aq. sodium thiosulfate solution (6 mL), and extracted with EtOAc. The organic layer was dried (MgSO4), filtered, and evaporated to afford the title compound (517 mg) as a light brown oil, which was directly used in the next step.

後処理

  1. additionafter 20 min the reaction mixture was poured onto water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-7ef7172636944e12b9986b5fd24a4f94
出典データセット
uspto-grants-2012_03
特許番号
US08138175B2

関連ノート

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