Ethyl Acetate → (4-Bromo-2-methoxy-6-nitro-phenyl)-(2-methoxy-ethyl)-amine

HRID 1661901Notes

Reaction equation

HRID 1661901 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:7]=1[O:15][CH3:16].[Br:17]Br.CCOC(C)=O>C(O)(=O)C>[Br:17][C:9]1[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[C:7]([O:15][CH3:16])[CH:8]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 57772036(2-Methoxy-ethyl)-(2-methoxy-6-nitro-phenyl)-amine

Product 1

HCID 57772042(4-Bromo-2-methoxy-6-nitro-phenyl)-(2-methoxy-ethyl)-amineYield 72.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of ca. 20 g (contains 15.65 g, 58.9 mmol) (2-methoxy-ethyl)-(2-methoxy-6-nitro-phenyl)-amine in 150 ml glacial acetic acid, 3.0 ml (58.9 mmol) bromine is slowly added at room temperature. The reaction mixture is stirred at room temperature for 3 h. 600 ml EtOAc are added and this solution is washed with 4n NaOH (2×), water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is recrystallized from diethyl ether/hexane to afford 13 g of the pure title compound as orange crystals and 6.6 g of an orange oil which contained 50% of the starting material.

Workup

  1. washthis solution is washed with 4n NaOH (2×), water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is recrystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-6c3ceda41b0e4778b2b8cd1c86df4233
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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