Potassium Carbonate → HCID 19837376, compound

HRID 1031394Notes

Reaction equation

HRID 1031394 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[OH:22].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:14][C:13]=1[O:22][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 27366032-Chloro-4-(trifluoromethyl)phenol

Product 1

HCID 19837376HCID 19837376, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 29.4 g (0.200 mol) of 2-fluoro nitrobenzene, 41.0 g (0.200 mol) of 2-chloro-4-trifluoromethylphenol and 30.0 g (0.220 mol) of K2CO3 in 150 ml of DMSO was heated at 100° C. for six hours. The reaction mixture was poured over ice and extracted with ether. The organic phase was washed with water and saturated aqueous NaCl and dried (MgSO4). The solvent was removed by evaporation at reduced pressure to yield 56.1 g (88%) of the desired product as a yellow oil. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. additionThe reaction mixture was poured over ice
  2. extractionextracted with ether
  3. washThe organic phase was washed with water and saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation at reduced pressure

Sources & evidence

ORD record
ord-57d05a1174d247588dedb3b4e03018c3
Source dataset
uspto-grants-1990_09
Patent number
US04954163

Reaction notes

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