Bromine → 5-Bromo-2-[2-methyl-3-(trifluoromethyl)anilino]benzoic acid

HRID 437197Notes

Reaction equation

HRID 437197 reaction equation
[Br:1]Br.[CH3:3][C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:5]=1[NH:14][C:15]1[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:17]([OH:19])=[O:18]>C(O)(=O)C>[Br:1][C:21]1[CH:20]=[C:16]([C:17]([OH:19])=[O:18])[C:15]([NH:14][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([F:11])([F:12])[F:13])[C:4]=2[CH3:3])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 20043403HCID 20043403, compound

Product 1

HCID 451177045-Bromo-2-[2-methyl-3-(trifluoromethyl)anilino]benzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Over a 30 minute period and with constant stirring, add 16 g. of bromine dissolved in 50 ml. of glacial acetic acid to a mixture of 37 g. of N-(2-methyl-3-trifluoromethylphenyl) anthranilic acid in 350 ml. of glacial acetic acid. Pour the resulting mixture into 1500 ml. of water, filter and dry the precipitate. Recrystallize the product from acetonitrile to obtain 5-bromo-N-(2-methyl-3-trifluoromethylphenyl) anthranilic acid, m.p. 223°-225° C.

Workup

  1. additionwith constant stirring, add 16 g
  2. additionPour the resulting mixture into 1500 ml
  3. filtrationof water, filter
  4. customdry the precipitate
  5. customRecrystallize the product from acetonitrile

Sources & evidence

ORD record
ord-c84d396420a5431894bb53f181768699
Source dataset
uspto-grants-1977_06
Patent number
US04029815

Reaction notes

Loading…