Acetyl chloride → HCID 117941925, compound

HRID 1499108Notes

Reaction equation

HRID 1499108 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N:9]1[CH:13]=[CH:12][C:11]([CH3:14])=[N:10]1.BrC1C=CC(Cl)=CC=1N1C(C)=CC=N1.C([Mg]Cl)(C)C.[C:34](Cl)(=[O:36])[CH3:35]>C1COCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:34](=[O:36])[CH3:35])=[C:3]([N:9]2[CH:13]=[CH:12][C:11]([CH3:14])=[N:10]2)[CH:4]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 131734237HCID 131734237, compound2×HCID 178418918HCID 178418918, compound

Product 1

HCID 117941925HCID 117941925, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-bromo-5-chlorophenyl)-3-methyl-1H-pyrazole/1-(2-bromo-5-chlorophenyl)-5-methyl-1H-pyrazole mixture (Intermediate 3, step 1) (1.00 g, 3.68 mmol) was dissolved in THF (6 mL) and cooled to 0° C. i-Propyl magnesium chloride (2.76 mL, 2.0 M in THF, 5.52 mmol) was added dropwise and allowed to warm to RT over 30 min. The reaction was then cooled to −15° C. Acetyl chloride (481 μL, 5.5 mmol) was added and the reaction was warmed to RT for 3 h. The reaction was quenched with HCl (2 N, 4 mL), then extracted with water and EtOAc, washed with brine, and dried over Na2SO4, filtered, and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtOAc/heptane) provided 1-[4-chloro-2-(3-methyl-pyrazol-1-yl)-phenyl]-ethanone.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction was then cooled to −15° C
  3. temperaturethe reaction was warmed to RT for 3 h
  4. customThe reaction was quenched with HCl (2 N, 4 mL)
  5. extractionextracted with water and EtOAc
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by normal phase silica gel column chromatography (EtOAc/heptane)

Sources & evidence

ORD record
ord-e852fd017c6242de841400e8709cb464
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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