Boron tribromide → 1-(4-hydroxyphenyl)-1H-pyrazole-4-carbonitrile

HRID 537531Notes

Reaction equation

HRID 537531 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[N:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[N:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 533021171-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 671200531-(4-hydroxyphenyl)-1H-pyrazole-4-carbonitrileYield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-methoxyphenyl)-1H-pyrazole-4-carbonitrile (115 mg, 0.575 mmol) in dichloromethane (5 mL) was added boron tribromide (431 mg, 1.73 mmol) at −10° C. The reaction was then warmed to room temperature and stirred for 16 hours. The reaction was quenched with methanol (0.5 mL) and water (5 mL), and extracted with ethyl acetate (3×15 mL). The combined organics were washed with brine (15 mL), dried over sodium sulfate, filtered and concentrated to give 1-(4-hydroxyphenyl)-1H-pyrazole-4-carbonitrile (46 mg, 43%) as a yellow solid. 1H NMR (400 MHz, CDCl3, δ): 9.89 (s, 1H), 9.12 (s, 1H), 8.27 (s, 1H), 7.62 (d, J=9.2 Hz, 2H), 6.90 (d, J=9.2 Hz, 2H).

Workup

  1. customThe reaction was quenched with methanol (0.5 mL) and water (5 mL)
  2. extractionextracted with ethyl acetate (3×15 mL)
  3. washThe combined organics were washed with brine (15 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b31e728bb31545bd97978edcc677f032
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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