Hydrochloric Acid → HCID 58153394, compound

HRID 508478Notes

Reaction equation

HRID 508478 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].Cl[C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][N:15]=2)=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 805204-Chloro-3-(trifluoromethyl)phenolHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 58153394HCID 58153394, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A 250 ml two-necked round-bottomed flask equipped with a magnetic bar, a thermometer and a reflux condenser is charged with DMF (30 ml), 4-chloro-3-trifluoromethyl-phenol (4.5 g), 2-chloro-4-methyl-5-nitro-pyridine (4.0 g) and potassium carbonate (6.4 g). The reaction mixture is stirred at ambient temperature for 1 hour, poured into water (300 ml), acidified with HCl 5 molar (15 ml) and then extracted with ethylacetate (4×50 ml). The combined organic layers are washed with brine (100 ml), dried over sodium sulfate, filtered and the solvent is removed in vacuo. Purification by flash chromatography over silica gel with hexane/ethyl acetate 7:3 (v:v) gives 7.03 g of the compound as a red solid (MP: 75-80° C.).

Workup

  1. customA 250 ml two-necked round-bottomed flask equipped with a magnetic bar
  2. extractionextracted with ethylacetate (4×50 ml)
  3. washThe combined organic layers are washed with brine (100 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customPurification by flash chromatography over silica gel with hexane/ethyl acetate 7:3 (v:v)

Sources & evidence

ORD record
ord-efae47a0fc03452ca08af62d4ec8ce25
Source dataset
uspto-grants-2015_08
Patent number
US09096525B2

Reaction notes

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