Sodium Bicarbonate → methyl 3-amino-2-bromo-5-fluorobenzoate

HRID 521411Notes

Reaction equation

HRID 521411 reaction equation
[Br:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][C:8]([F:14])=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[C:15]([O-])(O)=O.[Na+]>CCO.CC(O)=O.O.[Fe]>[NH2:11][C:10]1[C:2]([Br:1])=[C:3]([CH:7]=[C:8]([F:14])[CH:9]=1)[C:4]([O:6][CH3:15])=[O:5]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 86314150HCID 86314150, compound

Product 1

HCID 63022281methyl 3-amino-2-bromo-5-fluorobenzoateYield 87%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 18476134Acetic acid ethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-bromo-5-fluoro-3-nitrobenzoate (20 g, 278 mmol) in EtOH/CH3COOH (200 mL/200 mL) was added iron powder (25 g, 55 mmol). The mixture was vigorously stirred and heated to 85° C. for 1 h. After cooling, the mixture was diluted with water and basified with NaHCO3 (PH=8), extracted with ethyl acetate (450 ml×3). The combined organic layer was washed with brine (500 ml), dried over MgSO4, filtered, and evaporated in vacuum. The residue was applied to flash column chromatography (silica gel) to give methyl 3-amino-2-bromo-5-fluorobenzoate (15.6 g, 87%) as red oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (450 ml×3)
  3. washThe combined organic layer was washed with brine (500 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuum

Sources & evidence

ORD record
ord-c1785f6900dd47daabf7bfb883b28f7f
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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