Bromine → 2-Amino-5-bromo-4-chlorobenzoic acid

HRID 1910229

Reaction equation

HRID 1910229 reaction equation
[Br:1]Br.[NH2:3][C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]>C(O)(=O)C>[NH2:3][C:4]1[CH:12]=[C:11]([Cl:13])[C:10]([Br:1])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 24408BromineHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 196120502-Amino-5-bromo-4-chlorobenzoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 2.65 mL (52.0 mmol) of bromine in 10 mL of acetic acid was added dropwise over 15 minutes to a solution of 8.89 g (52.0 mmol) of 2-amino-4-chloro-benzoic acid in 60 mL of acetic acid. The mixture was stirred at room temperature for 1 h and poured into 500 grams of ice. The solid was collected by filtration, washed with cold water and dried to produce 11.2 g (86%) of 2-amino-5-bromo-4-chloro-benzoic acid. LCMS: 251 (M+1)+.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with cold water
  3. customdried

Sources & evidence

ORD record
ord-10d4a5404dcb499d99d66a2decc41c12
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Linked notes

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