Cesium fluoride → HCID 18319180, compound

HRID 1700999Notes

Reaction equation

HRID 1700999 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[C:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)#[N:13].[F-].[Cs+]>COCCOC.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[CH3:11])=[CH:16][CH:15]=1)#[N:13]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 2516721-Bromo-2-methyl-4-nitrobenzeneHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 18319180HCID 18319180, compoundYield 125.7%

Reagents, catalysts & solvents 2

HCID 80271Tri-o-tolylphosphineCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-bromo-5-nitrotoluene (7.05 gm, 32.67 mmol), 4-cyanophenylboronic acid (Tet. Lett., 1993, 34, 8237)(6.0 gm, 40.83 mmol), caesium fluoride (11.02 gm, 72.53 mmol) and tri-(2-methylphenyl)phosphine (1.0 gm, 3.27 mmol) in 1,2-dimethoxyethane (240 mL) were stirred under an atmosphere of nitrogen at room temperature for 40 mins. Tris(dibenzylideneacetone)dipalladiumn (1.50 gm, 1.63 mmol) was added and stirred for 10 mins at room temperature, then heated at 80° C. for 4 h. After being cooled, the mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was separated, washed with water, then dried (Na2SO4) and concentrated under reduced pressure to give crude 1-(4-cyanophenyl)-2-methyl-4-nitrobenzene (9.78 gm) which was used without further purification.

Workup

  1. stirringstirred for 10 mins at room temperature
  2. temperatureheated at 80° C. for 4 h
  3. temperatureAfter being cooled
  4. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. customThe organic phase was separated
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-626f2f455ac4431f81fc64664c6fd7bd
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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