Sodium Carbonate → 4-bromo-1-cyclopentyl-1H-pyrazole

HRID 1930390Notes

Reaction equation

HRID 1930390 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH:7]1([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)[CH2:11][CH2:10][CH2:9][CH2:8]1.[Br:17]Br>>[Br:17][C:15]1[CH:14]=[N:13][N:12]([CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:16]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 108444351-cyclopentyl-1H-pyrazole

Product 1

HCID 518921224-bromo-1-cyclopentyl-1H-pyrazoleYield 93%

Procedure

To a suspension of Na2CO3 (13 g, 124 mmol) in CH2OH2 (100 mL) was added 1-cyclopentyl-1 H-pyrazole (8.35 g, 62 mmol) and Br2 (3.2 mL). The resulting mixture was stirred at RT overnight. The solid was removed by filtration and the filter cake was washed with DCM. The combined filtrates were washed with water, brine and dried over anhydrous MgSO4. The solvent was concentrated to dryness to give 4-bromo-1-cyclopentyl-1 H-pyrazole (14 g, 93%). 1H NMR (300 MHz, CDCl3): δ7.46 (s, 1 H), 7.44 (s, 1 H), 4.64 (m, 1 H), 2.18-1.67(m, 8 H); MS (ESI) m/z: 215.0 [M+H]+.

Workup

  1. customThe solid was removed by filtration
  2. washthe filter cake was washed with DCM
  3. washThe combined filtrates were washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationThe solvent was concentrated to dryness

Sources & evidence

ORD record
ord-7b1c5c2509e24f45b6a7a68fa771ec5e
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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