Acetic Acid → 4-(2-Acetyl-3-oxobut-1-en-1-yl)-3-fluorobenzonitrile

HRID 1951392Notes

Reaction equation

HRID 1951392 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=O)[C:5]#[N:6].[CH3:12][C:13](=[O:18])[CH2:14][C:15](=[O:17])[CH3:16].C(O)(=O)C.N1CCCCC1>ClCCl.C1CCCCC1.C(OCC)(=O)C>[C:15]([C:14]([C:13](=[O:18])[CH3:12])=[CH:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[F:1])(=[O:17])[CH3:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 31261AcetylacetoneHCID 27831503-Fluoro-4-formylbenzonitrile

Product 1

HCID 674169264-(2-Acetyl-3-oxobut-1-en-1-yl)-3-fluorobenzonitrileYield 83.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

120 mg (0.805 mmol) of 3-fluoro-4-formylbenzonitrile, 80.6 mg (0.805 mmol) of 2,4-pentanedione, 72.5 mg (1.21 mmol) of acetic acid and 14 mg (0.16 mmol) of piperidine are dissolved in 8 ml of dichloromethane and heated under reflux with an inverse water trap overnight. The mixture shows complete conversion (TLC check, mobile phase: cyclohexane/ethyl acetate 5:1). The mixture is diluted with dichloromethane, washed with water and saturated sodium chloride solution and dried with sodium sulfate. The solvent is removed in a rotary evaporator. 155 mg (83.3% of theory) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-fluorobenzonitrile are obtained and are reacted without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux with an inverse water trap overnight
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. customThe solvent is removed in a rotary evaporator

Sources & evidence

ORD record
ord-cd84e51a10c44e48aaaa3e3aa3a6a3c3
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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