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

HRID 537531노트

반응식

HRID 537531 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b31e728bb31545bd97978edcc677f032
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859591B2

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