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

HRID 1401954Notes

Reaction equation

HRID 1401954 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-281756a30ccb4471aabe1844289a63c9
Source dataset
uspto-grants-2014_12
Patent number
US08907101B2

Reaction notes

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