Hydrochloric Acid → 2-Iodo-1-methyl-4-(methylsulfonyl)benzene

HRID 2390119노트

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HRID 2390119 반응식
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:5][C:3]=1N.Cl.N([O-])=O.[Na+].[I-:18].[K+]>O.CCOC(C)=O>[I:18][C:3]1[CH:5]=[C:6]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=[CH:8][C:2]=1[CH3:1]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 175119545-Methanesulfonyl-2-methylaniline2회HCID 23668193Sodium Nitrite

생성물 1

HCID 585220622-Iodo-1-methyl-4-(methylsulfonyl)benzene수율 73.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A cooled (0° C.) solution of 2-methyl-5-(methylsulfonyl)aniline (Intermediate 16; 556 mg; 3.00 mmol) in aqueous hydrogen chloride (5 M, 10 mL; 50 mmol) was treated with sodium nitrite (248 mg; 3.60 mmol) and the resulting mixture was stirred at 0° C. for 30 minutes, before being treated with a solution of potassium iodide (4.98 g; 30 mmol) in water (8 mL). The resulting mixture was stirred at RT for 1 hour, the EtOAc was added and the phases separated. The organic layer was washed twice with an aqueous, saturated sodium thiosulfate solution, then with brine, dried over MgSO4 and concentrated to afford a residue which was purified by column chromatography, eluting with cyclohexane containing increasing amounts of EtOAc to afford the title compound (649 mg, 73%) as a colorless liquid.

후처리

  1. stirringThe resulting mixture was stirred at RT for 1 hour
  2. customthe phases separated
  3. washThe organic layer was washed twice with an aqueous, saturated sodium thiosulfate solution
  4. dry with materialwith brine, dried over MgSO4
  5. concentrationconcentrated
  6. customto afford a residue which
  7. customwas purified by column chromatography
  8. washeluting with cyclohexane containing
  9. temperatureincreasing amounts of EtOAc

출처 및 근거

ORD 기록
ord-46e2034a46d44cd396422d01d7727824
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273769B2

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