Boron tribromide → HCID 67120046, compound

HRID 242208Notes

Reaction equation

HRID 242208 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[O:11][CH:12]=[CH:13][C:14]=2[CH3:15])[N:5]([C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)[N:4]=1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[O:11][CH:12]=[CH:13][C:14]=2[CH3:15])[N:5]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67120069HCID 67120069, compound

Product 1

HCID 67120046HCID 67120046, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-ethyl-1-(4-methoxyphenyl)-5-(3-methylfuran-2-yl)-1H-pyrazole-4-carbonitrile (5 mg, 0.02 mmol) was dissolved in CH2Cl2 (3 mL) and BBr3 (1 M solution on DCM, 0.3 mL, 0.3 mmol) was added and stirred at room temperature over night. The reaction was quenched using water and extracted with CH2Cl2. Concentration gave a crude 3-ethyl-1-(4-hydroxyphenyl)-5-(3-methylfuran-2-yl)-1H-pyrazole-4-carbonitrile (5 mg, 0.02 mmol, 100%) which was used as such in the next step.

Workup

  1. customThe reaction was quenched
  2. extractionextracted with CH2Cl2
  3. concentrationConcentration

Sources & evidence

ORD record
ord-443fc0962d96469eb89603e64aea7009
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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