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

HRID 507038ノート

反応式

HRID 507038 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回HCID 656671Sodium Pyrosulfite溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-6ef97865e4da4265acbc33d23ec58cbc
出典データセット
uspto-grants-2010_08
特許番号
US07786108B2

反応ノート

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