Bromine → 3-bromo-4H,5H,6H-pyrrolo[1,2-b]pyrazole

HRID 1504793Notes

Reaction equation

HRID 1504793 reaction equation
[N:1]1[N:2]2[CH2:8][CH2:7][CH2:6][C:3]2=[CH:4][CH:5]=1.C([O-])(=O)C.[Na+].[Br:14]Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:14][C:4]1[CH:5]=[N:1][N:2]2[CH2:8][CH2:7][CH2:6][C:3]=12

Participants

6

Reactant 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 110733655,6-Dihydro-4H-pyrrolo(1,2-b)pyrazole

Product 1

HCID 152870713-bromo-4H,5H,6H-pyrrolo[1,2-b]pyrazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (47.2 g, 437 mmol) and sodium acetate (36.2 g, 440 mmol) in acetic acid (750 mL) at 0° C. was added bromine (22.4 mL, 435 mmol). After 10 minutes, the reaction mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (5×200 mL). The organic layers were combined, dried over magnesium sulfate, and concentrated under reduced pressure to afford 3-bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole.

Workup

  1. extractionextracted with ethyl acetate (5×200 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47f2f55f28374be6a754d04da8a619a6
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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