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

HRID 46287

반응식

HRID 46287 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c2524a5135f547338c10b1fc44b5fda2
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

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