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

HRID 913896

反応式

HRID 913896 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 575461423-Bromo-2-iodo-5-(trifluoromethyl)aniline

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-24bf3eb8f2554ac5ae473672e1b1b61d
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

関連ノート

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