(1,1'-Biphenyl)-2-ol → 2-(Biphenyl-2-yloxy)-5-bromo-benzonitrile

HRID 46287

反応式

HRID 46287 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[C:11]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:17]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[C:7]#[N:8]

参加物

5

反応物 3

HCID 7017(1,1'-Biphenyl)-2-olHCID 11430Potassium CarbonateHCID 27249005-Bromo-2-fluorobenzonitrile

生成物 1

HCID 594365902-(Biphenyl-2-yloxy)-5-bromo-benzonitrile収率 89%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A suspension of 5-bromo-2-fluorobenzonitrile (6.48 g, 32.4 mmol), 2-phenylphenol (5.79 g, 34 mmol) and potassium carbonate (4.92 g, 35.6 mmol) in DMF (50 ml) was heated at 70° C. for 3 hours. The reaction was cooled and quenched by the addition of water (200 ml) followed by extraction with tBuOMe. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified using silica gel column chromatography (ethyl acetate:Heptane 5:95 to 15:85) to furnish 10.1 g of the desired compound. LCMS Rt=1.78 min MS m/z 349 [M]+1HNMR (d6-DMSO): δ 6.6 (m, 1H), 7.2-7.6 (m, 9H), 7.65 (m, 1H), 8.0 (m, 1H).

後処理

  1. temperatureThe reaction was cooled
  2. customquenched by the addition of water (200 ml)
  3. extractionfollowed by extraction with tBuOMe
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

出典と根拠

ORDレコード
ord-c2524a5135f547338c10b1fc44b5fda2
出典データセット
uspto-grants-2013_09
特許番号
US08541588B2

関連ノート

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