Potassium Phosphate, Tribasic → 5-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-pyrazole

HRID 2172280Notes

Reaction equation

HRID 2172280 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1I.[CH3:13][N:14]1[C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=[N:15]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:18]1[N:14]([CH3:13])[N:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 467352311-Bromo-2-iodo-4-(trifluoromethyl)benzene

Product 1

HCID 712595845-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-pyrazoleYield 57.1%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

A 75-mL pressure vessel was charged with 1-bromo-2-iodo-4-(trifluoromethyl)benzene (2.015 g, 5.74 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Aldrich, St. Louis, Mo., 1.374 g, 6.60 mmol), potassium phosphate (2.438 g, 11.48 mmol), and PdCl2(dppf)-CH2Cl2 adduct (Strem Chemicals Inc., Newburyport, Mass., 0.469 g, 0.574 mmol). The vessel was flushed with Ar (g), then DMF (19.14 ml) was added. The vial was sealed and placed in an 80° C. oil bath for 2 hours. The mixture was diluted with water and extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on an 80 g silica gel column to give 5-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-pyrazole (1.001 g, 3.28 mmol) as a yellow solid. [M+H]+=307.0.

Workup

  1. customThe vessel was flushed with Ar (g)
  2. additionDMF (19.14 ml) was added
  3. customThe vial was sealed
  4. customplaced in an 80° C.
  5. customfor 2 hours
  6. additionThe mixture was diluted with water
  7. extractionextracted with EtOAc (3×)
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was chromatographed on an 80 g silica gel column

Sources & evidence

ORD record
ord-5b344cc8d2564618a8019aca3f0341eb
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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