Boron tribromide → 2-(1H-pyrazol-4-yl)phenol

HRID 1581808Notes

Reaction equation

HRID 1581808 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[N:11][NH:12][CH:13]=1.B(Br)(Br)Br>ClCCl>[NH:11]1[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[OH:2])[CH:13]=[N:12]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 227234704-(2-Methoxyphenyl)-1H-pyrazole

Product 1

HCID 227234562-(1H-pyrazol-4-yl)phenolYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(2-methoxyphenyl)pyrazole (300 mg, 1.72 mmol) in dichloromethane (13 ml) is added a 1M solution of boron tribromide (3.8 ml) in dichloromethane. The mixture is stirred at room temperature over night then concentrated under reduced pressure. The residue is chromatographed (silica gel, dichloromethane/ethanol 9:1) to give 270 mg of 2-(pyrazol-4-yl)phenol (98%).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue is chromatographed (silica gel, dichloromethane/ethanol 9:1)

Sources & evidence

ORD record
ord-dfe1e48f283d449cb79bdc8f3c9fde14
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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