Chloroacetic Acid → N-(4-Bromo-2-carboxyphenyl)glycine

HRID 239008Notes

Reaction equation

HRID 239008 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[CH2:13][C:14]([OH:16])=[O:15].CCOCC.Cl>C([O-])([O-])=O.[Na+].[Na+]>[C:14]([CH2:13][NH:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 798582-Amino-5-bromobenzoic acid

Product 1

HCID 95158N-(4-Bromo-2-carboxyphenyl)glycineYield 60%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino-5-bromobenzoic acid (2 g, 9 mmol) in 15 ml of 2 N Na2CO3, a solution of chloroacetic acid (0.69 g, 7.3 mmol) in 7.5 ml of 2 N Na2CO3 was slowly added dropwise. Then, after stirred for 20 hours at 80° C., the reaction mixture was cooled down to room temperature. 50 ml of ether and 8 ml of 2 N hydrochloric acid were added to the mixture. The organic phase was separated, and dried with MgSO4. After evaporation, a light brown solid was obtained. The solid was purified by silica gel column chromatography (ethyl acetate/methanol, v/v, 1/1) to obtain a white solid (2-(N-carboxymethylamino)-5-bromobenzoic acid) (1.55 g, yield: 60%; mp: 178-180° C.).

Workup

  1. temperaturethe reaction mixture was cooled down to room temperature
  2. customThe organic phase was separated
  3. dry with materialdried with MgSO4
  4. customAfter evaporation
  5. customa light brown solid was obtained
  6. customThe solid was purified by silica gel column chromatography (ethyl acetate/methanol, v/v, 1/1)

Sources & evidence

ORD record
ord-f686028a6bd84ae98f434727a7e29d64
Source dataset
uspto-grants-2014_02
Patent number
US08642765B2

Reaction notes

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