Hydrochloric Acid → 1-(4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone

HRID 1499101Notes

Reaction equation

HRID 1499101 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N:9]1[CH:13]=[CH:12][C:11]([CH3:14])=[N:10]1.C([Mg]Cl)(C)C.[F:20][C:21]([F:28])([F:27])[C:22](OCC)=[O:23].Cl>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:22](=[O:23])[C:21]([F:28])([F:27])[F:20])=[C:3]([N:9]2[CH:13]=[CH:12][C:11]([CH3:14])=[N:10]2)[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 1179420861-(2,5-dibromophenyl)-3-methyl-1H-pyrazoleHCID 178418918HCID 178418918, compound

Product 1

HCID 1179421121-(4-Bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2,5-dibromophenyl)-3-methyl-1H-pyrazole (23.0 g, 73 mmol) from Step 1 was dissolved in 200 mL of THF and cooled to 0° C. i-Propyl magnesium chloride (2.0 M in THF, 40 mL) was added dropwise and the reaction was stirred for 45 min, then ethyl trifluoroacetate (10.5 mL) was added. The reaction was stirred for 30 min at 0° C., then 10% HCl is added dropwise (400 mL). The reaction was extracted with water and EtOAc, washed with brine, dried over Na2SO4, filtered, and then concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtOAc/heptane) provided 1-(4-bromo-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction was stirred for 30 min at 0° C.
  3. extractionThe reaction was extracted with water and EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by normal phase silica gel column chromatography (EtOAc/heptane)

Sources & evidence

ORD record
ord-35702ffc0b514c24858ee1ea97790ccf
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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