Pyridine → HCID 22148146, compound

HRID 1823952Notes

Reaction equation

HRID 1823952 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 72452-ChlorophenolHCID 27343253-Cyanophenylboronic acid

Product 1

HCID 22148146HCID 22148146, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 3-cyanophenyl boronic acid (2.84 g, 19.3 mmol), 2-chlorophenol (1.24 g, 9.64 mmol), copper (II) acetate (1.75 g, 9.64 mmol) and 4 Å molecular sieves is added CH2Cl2 (30 mL). While stirring at 25° C., pyridine (3.89 mL, 48.2 mmol) of is added and the reaction mixture stirred at 25° C. for 48 hours. Once complete, the reaction is filtered, and the resulting filtrate is concentrated to afford a crude oil which is purified by column chromatography (5% ethyl acetate in hexanes) to provide 1.92 g of 3-(2-chlorophenoxy)benzonitrile.

Workup

  1. stirringthe reaction mixture stirred at 25° C. for 48 hours
  2. filtrationOnce complete, the reaction is filtered
  3. concentrationthe resulting filtrate is concentrated
  4. customto afford a crude oil which
  5. customis purified by column chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f78e9f3b6fb64baea87c1e8f2a912768
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

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