Ammonium Hydroxide → HCID 1510471, compound

HRID 708941Notes

Reaction equation

HRID 708941 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-9806c5e31c3f4d41a4a679b1b9d120a1
Source dataset
uspto-grants-2015_11
Patent number
US09179681B2

Reaction notes

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