Acetic Acid → 4-Bromo-3-fluoro-6-iodo-2-methoxy-5-methylphenylamine

HRID 17301Notes

Reaction equation

HRID 17301 reaction equation
[I:1]N1C(=O)CCC1=O.C(O)(=O)C.[Br:13][C:14]1[C:20]([CH3:21])=[CH:19][C:17]([NH2:18])=[C:16]([O:22][CH3:23])[C:15]=1[F:24]>[Cl-].[Na+].O>[Br:13][C:14]1[C:20]([CH3:21])=[C:19]([I:1])[C:17]([NH2:18])=[C:16]([O:22][CH3:23])[C:15]=1[F:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 120273N-IodosuccinimideHCID 860974514-Bromo-3-fluoro-2-methoxy-5-methylaniline

Product 1

HCID 860974524-Bromo-3-fluoro-6-iodo-2-methoxy-5-methylphenylamine

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

N-iodosuccinimide (1.91 g, 8.5 mmol) was added to an acetic acid (40 ml) solution of 4-bromo-3-fluoro-2-methoxy-5-methylaniline (I-43) (1.90 g, 8.1 mmol), followed by stirring at room temperature for 67 hours. Saturated brine was added to the reaction liquid, followed by extraction twice with ethyl acetate, the organic layer was washed three times with saturated brine, dried over anhydrous magnesium sulfate.

Workup

  1. extractionfollowed by extraction twice with ethyl acetate
  2. washthe organic layer was washed three times with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-3933087f8a4a4ed49b2bc3f566af531a
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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