4-Bromo-2-fluorophenol → 3'-Fluoro-4'-hydroxy[1,1'-biphenyl]-4-carbonitrile

HRID 1167858ノート

反応式

HRID 1167858 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].Br[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[CH:14]=1.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC(O)C.O>[F:20][C:15]1[CH:14]=[C:13]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:18]=[CH:17][C:16]=1[OH:19]

参加物

5

反応物 3

HCID 27249814-Bromo-2-fluorophenolHCID 27343264-Cyanophenylboronic acidHCID 22031701Potassium phosphate, tribasic, monohydrate

生成物 1

HCID 222745023'-Fluoro-4'-hydroxy[1,1'-biphenyl]-4-carbonitrile収率 55%

試薬・触媒・溶媒 1

HCID 21889133Propan-2-ol--water (1/1)溶媒

反応条件

温度
70 °C

実験手順

4-Cyanophenylboronic acid (0.92 g, 6.26 mmol), 4-bromo-2-fluorophenol (1.0 g, 5.2 mmol), potassium phosphate tribasic monohydrate (3.0 g, 15.6 mmol) and Pd (Ph3P)2Cl2 (73.0 mg, 0.1 mmol) were combined in a mixture of IPA/H2O (40 mL, 3:1) and heated at 70° C. After 2 hours, the mixture was allowed to cool to room temperature and was filtered over celite. The filtrate was diluted with 150 ml of CH2Cl2 and washed with water twice. The organic phase was dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was chromatographed over silica gel using CH2Cl2 to provide the title compound as a white powder (0.61 g, 55% yield). 1HNMR (300 MHz, CDCl3) δ5.20 (bs, 1H), 7.15-7.78 (m, 7H); MS (DCI) m/z 214 (M+H)+.

後処理

  1. temperatureto cool to room temperature
  2. filtrationwas filtered over celite
  3. additionThe filtrate was diluted with 150 ml of CH2Cl2
  4. washwashed with water twice
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was chromatographed over silica gel

出典と根拠

ORDレコード
ord-50676dfa89ad41b2bcc41fb8b6c0490f
出典データセット
uspto-grants-2003_09
特許番号
US06620839B2

反応ノート

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