Bromide ion → 1-[3-(2-Methyl-[1,3]dioxolan-2-yl)-benzyl]-4-nitro-1H-pyrazole

HRID 2064982Notes

Reaction equation

HRID 2064982 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=2)[CH2:12]OS(C)(=O)=O)[O:8][CH2:7][CH2:6][O:5]1.[N+:21]([C:24]1[CH:25]=[N:26][NH:27][CH:28]=1)([O-:23])=[O:22].C([O-])([O-])=O.[K+].[K+].[Br-]>CC(C)=O>[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=2)[CH2:12][N:26]2[CH:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:28]=[N:27]2)[O:8][CH2:7][CH2:6][O:5]1

Participants

7

Reactant 5

HCID 259Bromide ionHCID 947NitrogenHCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 86649478(3-(2-Methyl-[1,3]dioxolan-2-yl)-phenyl)methyl methanesulfonate

Product 1

HCID 669287401-[3-(2-Methyl-[1,3]dioxolan-2-yl)-benzyl]-4-nitro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methanesulfonic acid 3-(2-methyl-[1,3]dioxolan-2-yl)-benzyl ester (220 mg, 0.81 mmol) and 4-nitro-1H-pyrazole (103 mg, 0.81 mmol) in acetone (8.0 mL) was treated with K2CO3 (564 mg, 4.04 mmol) followed by TBA bromide (48 mg, 0.15 mmol). The reaction mixture was stirred at rt for 16 h. The solvent was removed under reduced pressure. Water (10 mL) and EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (80:20 hept-EA) gave the title compound as a pale yellow solid. TLC: rf (50:50 hept-EA)=0.5. LC-MS-conditions 02: tR=0.97 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionWater (10 mL) and EA (10 mL) were added
  3. extractionThe aq. layer was extracted with EA (10 mL)
  4. dry with materialextracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (80:20 hept-EA)

Sources & evidence

ORD record
ord-687a8dabbc844f5ba9904d3742f30225
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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