Bromine → Ethyl 4-amino-3-bromo-5-nitrobenzoate

HRID 852608Notes

Reaction equation

HRID 852608 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[Br:16]Br>C(Cl)Cl>[NH2:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][C:12]=1[Br:16]

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 3018687Benzoic acid, 4-amino-3-nitro-, ethyl ester

Product 1

HCID 3019079Ethyl 4-amino-3-bromo-5-nitrobenzoateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-amino-3-nitrobenzoate (D212) (21.0 g, 100 mmol, 1 equiv) in CH2Cl2 (500 ml) at room temperature was added bromine (6.7 ml, 130 mmol, 1.3 equiv) and the resulting mixture was refluxed for 4 h then bromine (2 ml, 40 mmol, 0.4 equiv) was added and the resulting mixture refluxed for another 3 h then cooled to room temperature. The organic phase was washed twice with a 10% aqueous Na2S2O3 solution and twice with H2O, dried over MgSO4 and concentrated in vacuo to give ethyl 4-amino-3-bromo-5-nitrobenzoate (D213) (27.1 g, 94%) as a yellow solid which was used in the next step without further purification.

Workup

  1. temperaturethe resulting mixture was refluxed for 4 h
  2. temperaturethe resulting mixture refluxed for another 3 h
  3. washThe organic phase was washed twice with a 10% aqueous Na2S2O3 solution and twice with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-79ed2912926646e2a2f3706c971546e4
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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