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

HRID 1096193

반응식

HRID 1096193 반응식
[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]

참가 물질

9

반응물 6

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

생성물 1

HCID 667832122-Chloro-4-iodo-1-trifluoromethylbenzene수율 73.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7ef7172636944e12b9986b5fd24a4f94
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138175B2

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