Potassium Phosphate, Tribasic → HCID 10560279, compound

HRID 1955111Notes

Reaction equation

HRID 1955111 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH:9]1[CH:13]=[CH:12][N:11]=[N:10]1.[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1F>CS(C)=O.O>[F:14][C:15]1[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:20]=1[N:9]1[CH:13]=[CH:12][N:11]=[N:10]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 178418936HCID 178418936, compound

Product 1

HCID 10560279HCID 10560279, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A slurry of dibasic potassium phosphate, 38.0 g (0.218 mol), and 1H-1,2,3-triazol, 7.53 g (6.3 mL, 0.109 mol), in 325 mL dimethylsulfoxide was treated dropwise with 3,4-difluoronitrobenzene, 17.3 g (12.1 mL, 0.109 mol), with heating to 90° C. for 18 h. The mixture was cooled to room temperature, diluted with water (500 mL) and extracted with ethyl acetate (4×50 miL). Drying (Na2SO4) and concentrating in vacuo afforded a light yellow solid. This material was chromatographed over 600 g 230-400 mesh silica gel eluting with methylene chloride, 1% (v:v), 2% (v:v) and 5%(v:v) methanol-methylene chloride to afford 11.38 g (50%) of 3-Fluoro-1-nitro-4-(1H-1,2,3-triazol-1-yl)benzene as a light yellow solid, mp=123-124.5° C., along with 9.66 g (43%) of regioisomer 3-Fluoro-1-nitro-4-(2H-1,2,3-triazol-2-yl)benzene as a light yellow solid, mp 137-139° C.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (4×50 miL)
  3. dry with materialDrying (Na2SO4)
  4. concentrationconcentrating in vacuo
  5. customafforded a light yellow solid
  6. customThis material was chromatographed over 600 g 230-400 mesh silica gel eluting with methylene chloride, 1% (v:v), 2% (v:v) and 5%(v:v) methanol-methylene chloride

Sources & evidence

ORD record
ord-66225dd98a794f7691380ba3607198d2
Source dataset
uspto-grants-2000_09
Patent number
US06124334

Reaction notes

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