4-Fluorobenzoyl chloride → Tert-butyl 4-(2,4-difluorophenyl)-2-(4-fluorobenzamido)benzoate

HRID 1673429Notes

Reaction equation

HRID 1673429 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])[CH:22]=[CH:21][C:13]=1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)Cl>[F:32][C:26]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=1[C:23]1[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])=[C:12]([NH:11][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[CH:24]=1

Participants

6

Reactant 3

HCID 678794-Fluorobenzoyl chloride2×HCID 516892Sodium BicarbonateHCID 67342694Tert-butyl 2-amino-4-(2,4-difluorophenyl)benzoate

Product 1

HCID 67342274Tert-butyl 4-(2,4-difluorophenyl)-2-(4-fluorobenzamido)benzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Procedure

0.055 mL of triethylamine and 0.036 mL of 4-fluorobenzoyl chloride were added to 3.5 mL of methylene chloride solution containing 60 mg of tert-butyl 2-amino-4-(2,4-difluorophenyl)benzoate at room temperature sequentially and stirred at the same temperature for 1 hour. 0.014 mL of triethylamine and 0.012 mL of 4-fluorobenzoyl chloride were added to the reaction mixture at room temperature sequentially and stirred at the same temperature for 1 hour. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane: ethyl acetate=4:1] to obtain tert-butyl 4-(2,4-difluorophenyl)-2-(4-fluorobenzamido)benzoate.

Workup

  1. stirringstirred at the same temperature for 1 hour
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane: ethyl acetate=4:1]

Sources & evidence

ORD record
ord-7e78f27fb8734bbba55e65f0aaa68788
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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