Boron tribromide → HCID 20430698, compound

HRID 2413273Notes

Reaction equation

HRID 2413273 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12].C(=O)=O.C(Cl)Cl>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 133714805-Chloro-2-(4-methoxyphenylamino)benzoic acidHCID 21247280dichloromethane Drikold

Product 1

HCID 20430698HCID 20430698, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (250 ml, 0.8 molar) in methylene dichloride was added dropwise over a period of 70 minutes to a mixture of 25.1 g of 5-chloro-2-(4-methoxyphenylamino)benzoic acid and 125 ml of dry methylene dichloride cooled to -70° C. (Dry Ice/methylene dichloride). The cooling bath was removed and the reaction mixture stirred for about 20 hours. The volatile solvent was stripped off and water (400 ml) was added dropwise to the residue cooled in an ice bath. The mixture was then made basic by addition of potassium carbonate and then acidified with dropwise addition of hydrochloric acid. The solid was collected by filtration and dried to give 19.3 g of 5-chloro-2-(4-hydroxyphenylamino)benzoic acid.

Workup

  1. customThe cooling bath was removed
  2. additionwater (400 ml) was added dropwise to the residue
  3. temperaturecooled in an ice bath
  4. additionThe mixture was then made basic by addition of potassium carbonate
  5. additionacidified with dropwise addition of hydrochloric acid
  6. filtrationThe solid was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-24c2183c37be43e7af6d96555ff3b8d3
Source dataset
uspto-grants-1985_01
Patent number
US04496590

Reaction notes

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