Cesium carbonate → HCID 21914164, compound

HRID 1246059Notes

Reaction equation

HRID 1246059 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[O:22][CH3:23].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([C:3]1[CH:4]=[C:5]([C:15]2[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=[CH:13][C:14]=2[O:22][CH3:23])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 788702-Bromo-4-nitroanisoleHCID 27343253-Cyanophenylboronic acid

Product 1

HCID 21914164HCID 21914164, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

[1,1′Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane(II) (1.43 g) was added to a stirred mixture of 3-cyanophenylboronic acid (10.0 g, 61.8 mmol) and 2-bromo-4-nitroanisole (14.35 g, 62 mmol) in 2.0N cesium carbonate (92.7 mL, 185.4 mmol) and ethylene glycol dimethylether (200 mL). The flask was purged with nitrogen and heated at 90° C. (oil bath) for 4 hours. The mixture was allowed to cool to room temperature overnight, during which time the product precipitated from solution. The solid was collected on a Buchner funnel, washed with water and dried under reduced pressure to give 2-(3-cyanophenyl)-4-nitroanisole (15.7 g).

Workup

  1. customThe flask was purged with nitrogen
  2. temperatureto cool to room temperature overnight, during which time the product
  3. customprecipitated from solution
  4. customThe solid was collected on a Buchner funnel
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-542b591a6b3345e4b0cb9f6289b95097
Source dataset
uspto-grants-2006_10
Patent number
US07125892B2

Reaction notes

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