Acetonitrile → HCID 54147598, compound

HRID 2174356Notes

Reaction equation

HRID 2174356 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].CC#N.Br[CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C([O-])([O-])=O.[K+].[K+]>O>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][CH2:21][CH2:20][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)=[CH:10][CH:11]=1)[CH3:27]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 54147598HCID 54147598, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4′-cyano-4-hydroxybiphenyl (4.0 g, 20.5 mmol), MeCN (30 ml), ethyl 4-bromobutyrate (3.75 ml, 5.11 g, 26.2 mmol), and K2CO3 (3.86 g, 27.9 mmol) was stirred at 85° C. After 20 h water (150 ml) was added, and the product was extracted with AcOEt. The combined extracts were washed with brine, dried over MgSO4, and concentrated, to yield 6.91 g (100%) of 4-(4′-cyanobiphenyl-4-yloxy)butyric acid ethyl ester as an oil.

Workup

  1. extractionthe product was extracted with AcOEt
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ea5f71a7000448359480afd6b9b4e079
Source dataset
uspto-grants-2015_06
Patent number
US09061067B2

Reaction notes

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