Iodine chloride → 2-Iodo-4-methyl-5-(trifluoromethyl)aniline

HRID 507038노트

반응식

HRID 507038 반응식
[I:1]Cl.[CH3:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12].C(=O)(O)[O-].[Na+]>ClCCl.CO.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[I:1][C:9]1[CH:10]=[C:4]([CH3:3])[C:5]([C:11]([F:12])([F:13])[F:14])=[CH:6][C:7]=1[NH2:8]

참가 물질

7

반응물 3

HCID 24640Iodine chlorideHCID 516892Sodium BicarbonateHCID 27377154-Methyl-3-(trifluoromethyl)aniline

생성물 1

HCID 534211462-Iodo-4-methyl-5-(trifluoromethyl)aniline수율 103.1%

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매2회HCID 656671Sodium Pyrosulfite용매

실험 절차

Add a solution of iodine monochloride (27.8 g, 171 mmol) in dichloromethane (180 mL) to a solution of 4-methyl-3-trifluoromethylaniline (25.0 g, 143 mmol) and sodium bicarbonate (14.4 g, 171 mmol) in methanol (180 mL) and dichloromethane (730 mL) at room temperature under nitrogen. Stir the mixture for 3 h and dilute the cooled mixture with aqueous sodium metabisulfite (500 mL). Collect the organic phase, and extract the aqueous phase with methylene chloride (200 mL). Wash the combined organic extracts with brine (250 mL), dry over anhydrous sodium sulfate and filter. Remove the solvent under reduced pressure to provide a brown oil, which crystallizes upon standing to afford the title compound as brown needles (44.4 g, >99%), which is used in the next step without purification. APCI MS m/z 302 (M+H)+.

후처리

  1. customCollect the organic phase
  2. extractionextract the aqueous phase with methylene chloride (200 mL)
  3. washWash the combined organic extracts with brine (250 mL)
  4. dry with materialdry over anhydrous sodium sulfate
  5. filtrationfilter
  6. customRemove the solvent under reduced pressure
  7. customto provide a brown oil, which
  8. customcrystallizes

출처 및 근거

ORD 기록
ord-6ef97865e4da4265acbc33d23ec58cbc
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786108B2

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