Ammonium Hydroxide → HCID 1510471, compound

HRID 1192785Notes

Reaction equation

HRID 1192785 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.I[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH4+].[OH-]>CCOCC.[Cu]I.CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][C:15]([F:16])([F:17])[F:18])=[CH:12][CH:13]=2)[CH:6]=1

Participants

8

Reactant 4

HCID 14923Ammonium HydroxideHCID 163754-BromopyrazoleHCID 62657Potassium Phosphate, TribasicHCID 27772941-Iodo-4-(trifluoromethoxy)benzene

Product 1

HCID 1510471HCID 1510471, compoundYield 68.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

4-Bromopyrazole (1.5 g, 10 mmol) and 4-iodotrifluoromethoxybenzene (3.0 g, 10.3 mmol) were stirred DMF (8 mL) and treated with potassium phosphate (6.3 g, 30 mmol) and CuI (0.5 g, 2.6 mmol). The solution was stirred and heated to 130° C. for 30 min, then it was cooled to ambient temperature and poured into 1 N NH4OH (50 mL). The solid precipitate was isolated by filtration, re-dissolved in ether, filtered and concentrated to a tan solid. Recrystallization from EtOH gave an off-white solid (2.1 g): mp 63-65° C.; LCMS 308.6 (M+1).

Workup

  1. temperatureit was cooled to ambient temperature
  2. customThe solid precipitate was isolated by filtration
  3. filtrationfiltered
  4. concentrationconcentrated to a tan solid
  5. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-996cc3481d194154a2ff1a291f9fe143
Source dataset
uspto-grants-2014_03
Patent number
US08680269B2

Reaction notes

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