Potassium Carbonate → HCID 67032745, compound

HRID 876625Notes

Reaction equation

HRID 876625 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[Na+].Cl[C:20]([F:25])([F:24])C([O-])=O>CN(C=O)C.O.CCOC(C)=O>[F:24][CH:20]([F:25])[O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[I:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 186726022-Iodo-5-nitrophenol

Product 1

HCID 67032745HCID 67032745, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-iodo-5-nitrophenol (8.98 g), K2CO3 (18.7 g) and 2-chloro-2,2-difluoro-acetic acid sodium salt (5.17 g) in DMF-H2O (60-6 mL) was stirred at 110° C. for 3.5 h and at room temperature for 12 h. The mixture was diluted with EtOAc and washed with 1H HCl, saturated NaHCO3 aq., water and brine, and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (Hexane/EtOAc=9/1) to obtain compound aa4-1 (9.17 g) as a brown amorphous solid.

Workup

  1. washwashed with 1H HCl, saturated NaHCO3 aq., water and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (Hexane/EtOAc=9/1)
  5. customto obtain compound aa4-1 (9.17 g) as a brown amorphous solid

Sources & evidence

ORD record
ord-752a3b8c6cd94f12b9fe94d7a8e3c484
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

Loading…