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Citric Acid → 2-(5-Bromo-2-hydroxybenzamido)-4-phenylbenzoic acid

HRID 454577
Notes
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Reaction equation

HRID 454577 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:38]=[CH:37][C:36]([Br:39])=[CH:35][C:12]=1[C:13]([NH:15][C:16]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][C:17]=1[C:18]([O:20]C(C)(C)C)=[O:19])=[O:14])(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>CO.O1CCOCC1>[Br:39][C:36]1[CH:37]=[CH:38][C:11]([OH:10])=[C:12]([CH:35]=1)[C:13]([NH:15][C:16]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][C:17]=1[C:18]([OH:20])=[O:19])=[O:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 66990421Tert-butyl 2-(2-acetoxy-5-bromobenzamido)-4-phenylbenzoate

Product 1

HCID 585089632-(5-Bromo-2-hydroxybenzamido)-4-phenylbenzoic acidYield 70.2%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

Potassium carbonate (0.049 g) was added to a solution mixture of tert-butyl 2-(2-acetoxy-5-bromobenzamido)-4-phenylbenzoate (0.060 g) in methanol (1 mL) and dioxane (1 mL), followed by stirring at room temperature for 1 hour. A 10% aqueous solution of citric acid and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Trifluoroacetic acid (5 mL) was added to the obtained residue, followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and methanol was added to the obtained residue. The solid substance was collected by filtration to obtain 0.034 g of 2-(5-bromo-2-hydroxybenzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionTrifluoroacetic acid (5 mL) was added to the obtained residue
  6. stirringby stirring at room temperature for 2 hours
  7. customThe solvent was evaporated under reduced pressure, and methanol
  8. additionwas added to the obtained residue
  9. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-665663a03fa442a098e0e2cb54e8f76f
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492582B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes