Hydrochloric Acid → 4-Bromo-2-carboxybenzenepropanoic acid

HRID 2377226Notes

Reaction equation

HRID 2377226 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])([OH:3])=[O:2].[Br:15]Br.O.Cl>[N+]([O-])(O)=O>[Br:15][C:12]1[CH:13]=[CH:14][C:6]([CH2:5][CH2:4][C:1]([OH:3])=[O:2])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24408BromineHCID 2262943-(2-Carboxyphenyl)propionic acid

Product 1

HCID 692017574-Bromo-2-carboxybenzenepropanoic acid

Reagents, catalysts & solvents 1

HCID 944Nitric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2-(2-carboxyethyl)benzoic acid (5 g, 25.8 mmol) in 71% nitric acid (20 mL) in an amber vial was treated with bromine (1.3 mL, 25.8 mmol). The vial was capped and heated to about 90° C. for about 20 hours. The reaction was cooled, poured into water and 1M hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, dried (Na2SO4), filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol (20:1) as eluent to provide the desired product. MS (ESI): m/z 271, 273 (M−H)−.

Workup

  1. customThe vial was capped
  2. temperatureThe reaction was cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3412d519274f4143ae288fec1b822afe
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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