Ethanol → 5-Bromo-3-dibenzylamino-2-fluorobenzoic acid ethyl ester

HRID 1436717Notes

Reaction equation

HRID 1436717 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:27](O)[CH3:28]>S(=O)(=O)(O)O>[CH2:27]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]([N:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]=1[F:11])[CH3:28]

Participants

4

Reactant 2

HCID 702EthanolHCID 688175625-Bromo-3-dibenzylamino-2-fluorobenzoic acid

Product 1

HCID 688163695-Bromo-3-dibenzylamino-2-fluorobenzoic acid ethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Dissolve 5-bromo-3-dibenzylamino-2-fluorobenzoic acid (1.53 g, 3.69 mmol) in ethanol (40 mL). Add concentrated sulfuric acid (0.2 mL) as a catalyst and heat to at reflux for 1 day. Cool to room temperature and concentrate. Dissolve the residue in diethyl ether (30 mL) and wash with 10% aqueous potassium carbonate solution (10 mL) and water (10 mL). Dry (magnesium sulfate) and concentrate to give the title compound as an oil (1.50 g, 92%).

Workup

  1. temperatureheat
  2. temperatureto at reflux for 1 day
  3. concentrationconcentrate
  4. dissolutionDissolve the residue in diethyl ether (30 mL)
  5. washwash with 10% aqueous potassium carbonate solution (10 mL) and water (10 mL)
  6. dry with materialDry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-953452a1d57e42448d621f07398f5131
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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