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Oxalyl chloride → 2-Fluoro-N-(2-fluoro-3-hydroxy-6-methyl-phenyl)-5-(3-fluorophenyl)benzamide

HRID 1771627
Notes
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Reaction equation

HRID 1771627 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(C(Cl)=O)=O.[NH2:24][C:25]1[C:26]([F:33])=[C:27]([OH:32])[CH:28]=[CH:29][C:30]=1[CH3:31].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C.C1COCC1.O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([NH:24][C:25]1[C:30]([CH3:31])=[CH:29][CH:28]=[C:27]([OH:32])[C:26]=1[F:33])=[O:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 463123323',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acidHCID 894440343-Amino-2-fluoro-4-methylphenol

Product 1

HCID 894436192-Fluoro-N-(2-fluoro-3-hydroxy-6-methyl-phenyl)-5-(3-fluorophenyl)benzamideYield 60%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2 fluoro-5-(3-fluorophenyl) benzoic acid (intermediate III(a)) (730 mg, 3.1 mmol, 1.1 eq) and (COCl)2 (1.1 g, 8.49 mmol, 3 eq) in DCM (20 mL) was added DMF (5 drops). The reaction mixture was stirred at 0° C. for 1h and then concentrated in vacuo. The residue obtained was dissolved in THF (5 mL) and added dropwise to a solution of 3-amino-2-fluoro-4-methyl-phenol (400 mg, 2.83 mmol, 1 eq) 25 and NaHCO3 (951 mg, 11.3 mmol, 4 eq) in THF (15 mL) at 0° C. After the addition, the reaction mixture was stirred at room temperature for 3h. The resulting mixture was poured into water and extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4) to give the title compound as a yellow solid (600 mg, 60%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. additionAfter the addition
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:4)

Sources & evidence

ORD record
ord-1fd639b3f6e84ca484a80f2b5fa67afa
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249085B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes