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

HRID 1520908노트

반응식

HRID 1520908 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-b13a9eb59af544ea83189249f96f86b4
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073871B2

반응 노트

불러오는 중…