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

HRID 1892751ノート

反応式

HRID 1892751 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a6f2743bb3c849e8b45e2bdda0ee78b7
出典データセット
uspto-grants-2013_08
特許番号
US08507533B2

反応ノート

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