Potassium Carbonate → HCID 13409498, compound

HRID 1077982Notes

Reaction equation

HRID 1077982 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].F[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:23]([C:14]1[CH:15]=[C:16]([C:19]([F:20])([F:21])[F:22])[CH:17]=[CH:18][C:13]=1[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10])([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11970(2-Hydroxyphenyl)acetic acidHCID 677784-Fluoro-3-nitrobenzotrifluoride

Product 1

HCID 13409498HCID 13409498, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-hydroxyphenylacetic acid (1.52 g, 0.01 mol), 4-fluoro-3-nitrobenzotrifluoride (2.09 g, 0.01 mol), potassium carbonate (2.76 g, 0.02 mol) in dimethylformamide (10 mL) was heated at 95° C. 16 h. The solvent was evaporated, the residue was acidified with dilute HCl, extracted with EtOAc, dried over anhydrous sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid). Recrystallization from EtOAc/hexane gave the title compound; mp 165°-167° C.

Workup

  1. custom16 h
  2. customThe solvent was evaporated
  3. extractionextracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid)
  8. customRecrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-4f819c8f57654659a09c4fe5c17d9418
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

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