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

HRID 913896

Reaction equation

HRID 913896 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-24bf3eb8f2554ac5ae473672e1b1b61d
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Linked notes

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