Bromine → Ethyl 3-bromo-2-hydroxy-5-nitrobenzoate

HRID 1458208Notes

Reaction equation

HRID 1458208 reaction equation
[N+:1]([C:4]1[CH:14]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:7]([OH:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])(=O)C.[K+].[Br:21]Br>C(O)(=O)C>[Br:21][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:14]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:7]=1[OH:15]

Participants

5

Reactant 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 12512105HCID 12512105, compound

Product 1

HCID 15907522Ethyl 3-bromo-2-hydroxy-5-nitrobenzoateYield 100.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.74 kg (8.2 mol) of ethyl 5-nitrosalicylate and 700 g of potassium acetate were dissolved in 5000 ml of acetic acid. 1.312 kg of bromine was dropwise added to the obtained solution at room temperature in one hour. Thereafter, the resulting mixture was further stirred for one hour and then concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate. The obtained solution was washed with water, dehydrated and concentrated under reduced pressure. The obtained residue was crystallized from isopropyl ether to give 2.38 kg of the title compound as a colorless crystal.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe obtained residue was dissolved in ethyl acetate
  3. washThe obtained solution was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-ca00bac19ce34d849d42d1f31f97f4ec
Source dataset
uspto-grants-1998_12
Patent number
US05849912

Reaction notes

Loading…