Phosphorus tribromide → HCID 67120035, compound

HRID 242182Notes

Reaction equation

HRID 242182 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=O)[CH2:12][C:11]([CH2:15][CH2:16][CH3:17])=[N:10]2)=[CH:5][CH:4]=1.P(Br)(Br)[Br:19]>CC#N>[Br:19][C:13]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=[C:11]([CH2:15][CH2:16][CH3:17])[CH:12]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 142312202,4-Dihydro-2-(4-methoxyphenyl)-5-propyl-3H-pyrazol-3-one

Product 1

HCID 67120035HCID 67120035, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

1-(4-Methoxyphenyl)-3-propyl-1H-pyrazol-5(4H)-one (495 mg, 2.13 mmol) was put in a microwave tube and closed, MeCN (2.1 mL) and PBr3 (6.4 mL, 68.2 mmol) were added via syringe and the reaction was stirred at 150° C. for 40 min in the microwave. The product poured onto ice and was extracted with EtOAc. The organic phase was separated from the water phase and evaporated. The crude product was purified on silica column (CH2Cl2/Et2O, 1:1) to give 5-bromo-1-(4-methoxyphenyl)-3-propyl-1H-pyrazole (287 mg, 46%).

Workup

  1. customclosed
  2. additionThe product poured onto ice
  3. extractionwas extracted with EtOAc
  4. customThe organic phase was separated from the water phase
  5. customevaporated
  6. customThe crude product was purified on silica column (CH2Cl2/Et2O, 1:1)

Sources & evidence

ORD record
ord-17384bf2618e441eb29c36dffb2b0520
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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