Boron tribromide → 4-[(Biphenyl-4-carbonyl)-amino]-2-hydroxy benzoic acid

HRID 18444Notes

Reaction equation

HRID 18444 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([O:19]C)[CH:11]=2)=[O:8])=[CH:3][CH:2]=1.B(Br)(Br)Br>C(Cl)(Cl)Cl.[Cl-].[Na+].O>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:2]=[CH:3][C:4]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([OH:19])[CH:11]=2)=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 25134Boron tribromide2×HCID 10066264HCID 10066264, compound

Product 1

HCID 104494744-[(Biphenyl-4-carbonyl)-amino]-2-hydroxy benzoic acidYield 82.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4-[(biphenyl-4-carbonyl)amino]-2-methoxy benzoic acid (2.78 g; 8 mmol) in CHCl3 (175 mL) was cooled until it became cloudy (approx. 40° C.) and BBr3 (1.5 mL; 16 mmol) was added over 2 minutes. The mixture was allowed to warm slightly with stirring for 2 hours after which time another 1.5 mL BBr3 (16 mmol) was added and the reaction mixture was left to warm to room temperature overnight. The resulting slurry was added brine (50 mL) and the organic solvent was removed in vacuo. The resulting solid was Isolated by filtration, washed with H2O, air dried, refluxed in 99% EtOH (100 mL), cooled and filtered to yield 2.2 g (82%) of a white solid. Mp. 266° C. (decomposes).

Workup

  1. additionwas added over 2 minutes
  2. temperatureto warm slightly
  3. additionwas added
  4. waitthe reaction mixture was left
  5. customthe organic solvent was removed in vacuo
  6. customThe resulting solid was Isolated by filtration
  7. washwashed with H2O, air
  8. customdried
  9. temperaturerefluxed in 99% EtOH (100 mL)
  10. temperaturecooled
  11. filtrationfiltered

Sources & evidence

ORD record
ord-03ed0df505b74051954d225a4741e565
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Reaction notes

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