Bromine → Methyl 2-amino-5-bromo-4-chlorobenzoate

HRID 2353907Notes

Reaction equation

HRID 2353907 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH2:11].[Br:13]Br>CC(O)=O.C(OCC)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:13])[C:7]([Cl:10])=[CH:6][C:5]=1[NH2:11]

Participants

5

Reactant 2

HCID 24408BromineHCID 80001Methyl 4-chloroanthranilate

Product 1

HCID 53436879Methyl 2-amino-5-bromo-4-chlorobenzoateYield 78.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-Amino-4-chloro-benzoic acid methyl ester (1.85 g, 10.0 mmole) in HOAc (20.0 ml) was injected bromine (0.512 ml, 10.0 mmole) dropwise. The reaction was stirred at room temperature for an hour. The mixture was diluted with ethyl ether (200 ml) and then the solvents were decanted. The residue was partitioned between ethyl acetate (200 ml) and 0.100N NaOH(aq) (200 ml). After separated the two layers, the organic layer was dried over Na2SO4, filtered and concentrated to provide the crude product (2.08 g, 78%), which was used directly for the next step without further purification. MS (ES+): 264, 266 (M+H).

Workup

  1. customthe solvents were decanted
  2. customThe residue was partitioned between ethyl acetate (200 ml) and 0.100N NaOH(aq) (200 ml)
  3. customAfter separated the two layers
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4f2b11794c81424cb6028931f34bcb17
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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