N-Iodosuccinimide → 3-Bromo-2-iodo-5-(trifluoromethyl)aniline

HRID 931001

반응식

HRID 931001 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[I:13]N1C(=O)CCC1=O>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([I:13])=[C:4]([CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1)[NH2:5]

참가 물질

5

반응물 2

HCID 120273N-IodosuccinimideHCID 27358803-Bromo-5-(trifluoromethyl)aniline

생성물 1

HCID 575461423-Bromo-2-iodo-5-(trifluoromethyl)aniline수율 68.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-bromo-5-(trifluoromethyl)aniline (5.00 g) in acetic acid (40 mL) was added N-iodosuccinimide (5.16 g) at 0° C., and the mixture was stirred overnight at room temperature under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, washed with 10% aqueous sodium thiosulfate solution, saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (5.21 g). 1H NMR (300 MHz, CDCl3) δ 4.58 (2H, brs), 6.84 (1H, d, J=1.1 Hz), 7.23 (1H, d, J=1.1 Hz).

후처리

  1. washwashed with 10% aqueous sodium thiosulfate solution, saturated aqueous sodium bicarbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-4742f0dfcf32470bad86ff75ea01a13b
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296746B2

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