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

HRID 913896

반응식

HRID 913896 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)aniline

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

3-Bromo-5-(trifluoromethyl)aniline (20 g, 83 mmol) in acetic acid (150 ml) was treated portionwise with N-iodosuccinimide (20.62 g, 92 mmol). The reaction was stirred 24 h at ambient temperature. The reaction was diluted with ethyl acetate (600 mL) and was washed with aqueous sodium bisulfie (100 mL) and brine (100 mL). The organic layer was dried with magnesium sulfate and evaporated. The residue was purified on a silica gel column with a gradient of ethyl acetate/hexanes from 7% to 15% to give 23.5 g (77%) of slightly impure product. 1H-NMR (CDCl3, 400 MHz) δ 7.21 (d, J=1.3 Hz, 1H), 6.82 (d, J=1.5 Hz, 1H), 4.57 (bs, 2H); LC/MS (HPLC method 4): tR=3.578 min, 365.80(MH)+.

후처리

  1. washwas washed with aqueous sodium bisulfie (100 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. customevaporated
  4. customThe residue was purified on a silica gel column with a gradient of ethyl acetate/hexanes from 7% to 15%
  5. customto give 23.5 g (77%) of slightly impure product

출처 및 근거

ORD 기록
ord-24bf3eb8f2554ac5ae473672e1b1b61d
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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