4-Bromobenzophenone → 4-Benzoylbenzonitrile

HRID 2180655Notes

Reaction equation

HRID 2180655 reaction equation
[C-]#N.[Na+].Br[C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:7][CH:6]=1.[CH3:19][NH:20]CCNC.[OH-].[NH4+]>[Cu]I.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([C:19]#[N:20])=[CH:6][CH:7]=1)(=[O:12])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 70304-BromobenzophenoneHCID 8070N,N'-DimethylethylenediamineHCID 8929Sodium CyanideHCID 14923Ammonium Hydroxide

Product 1

HCID 739214-Benzoylbenzonitrile

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

An oven dried screw cap test tube was charged with NaCN (91 mg, 1.857 mmol), dried KI (51 mg, 0.307 mmol, 20 mol %), CuI (30 mg, 0.157 mmol, 10 mol %), (4-bromophenyl)-phenyl-methanone (404 mg, 1.548 mmol), evacuated and backfilled with argon three times. N,N′-dimethylethylenediamine (165 μL, 1.550 mmol) and anhydrous toluene (1 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min then the organic layer was washed with 1 mL of water and dried over MgSO4. The GC analysis showed complete conversion of starting material with formation of title product (confirmed by GC-MS).

Workup

  1. customAn oven dried screw
  2. customcap test tube
  3. customevacuated
  4. customThe tube was sealed
  5. temperatureThe resulting suspension was cooled to room temperature
  6. stirringThe mixture was stirred at 25° C. for 10 min
  7. washthe organic layer was washed with 1 mL of water
  8. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-a2aeb02fe6b84d77a474565dc63bbdad
Source dataset
uspto-grants-2005_05
Patent number
US06888032B2

Reaction notes

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