Pyridine → HCID 18792316, compound

HRID 1004533Notes

Reaction equation

HRID 1004533 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[C:6]([F:12])[C:7]=1[C:8]([F:11])([F:10])[F:9].N1C=CC=CC=1.C1(C)C=CC=CC=1.[F:27][C:28]1[CH:36]=[C:35]([CH2:37][CH2:38][CH3:39])[CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31]>O>[F:27][C:28]1[CH:36]=[C:35]([CH2:37][CH2:38][CH3:39])[CH:34]=[CH:33][C:29]=1[C:30]([O:13][C:4]1[CH:3]=[C:2]([F:1])[C:7]([C:8]([F:10])([F:11])[F:9])=[C:6]([F:12])[CH:5]=1)=[O:31]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140Toluene2×HCID 142098633,5-Difluoro-4-(trifluoromethyl)phenolHCID 184110222-Fluoro-4-propylbenzoyl chloride

Product 1

HCID 18792316HCID 18792316, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Then, 1.2 g (6.1 mmol) of 3,5-difluoro-4-trifluoromethyl-phenol, 0.7 ml of pyridine, and 2 ml of toluene were mixed. To this mixture was added dropwise 3 ml of toluene solution containing 6.1 mmol 2-fluoro-4-propylbenzoyl chloride at room temperature in 10 minutes. After the dropping was finished, they were reacted at 50° C. for 2 hours. After finishing of the reaction, 10 ml of water was added to the reaction product and then extracted with 30 ml of toluene. The organic layer thus obtained was washed with 6N-hydrochloric acid thrice, 2N-sodium hydroxide thrice, and water thrice, and then dried over anhydrous magnesium sulfate. Solvent was distilled off at a reduced pressure and the residue was subjected to a silica gel column chromatography (eluent: toluene) to obtain 2.0 g of a crude 3,5-difluoro-4-trifluormethylphenyl 2-fluoro-4-propylbenzoate. This product was recrystallized from a mixed solvent of heptane/ether (1/1) to obtain 1.1 g (yield: 50.2%) of the subject compound.

Workup

  1. customthey were reacted at 50° C. for 2 hours
  2. additionwas added to the reaction product
  3. extractionextracted with 30 ml of toluene
  4. customThe organic layer thus obtained
  5. washwas washed with 6N-hydrochloric acid thrice, 2N-sodium hydroxide thrice, and water thrice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationSolvent was distilled off at a reduced pressure

Sources & evidence

ORD record
ord-0c2f603a24354b049731c2223765eb4d
Source dataset
uspto-grants-2000_04
Patent number
US06051288

Reaction notes

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