4'-Fluoroacetophenone → HCID 54261868, compound

HRID 1647224Notes

Reaction equation

HRID 1647224 reaction equation
OS(C(F)(F)F)(=O)=O.C1([Si](C2C=CC=CC=2)(C)C)C=CC=CC=1.C(N(C(C)C)CC)(C)C.[F:33][C:34]1[CH:39]=[CH:38][C:37]([C:40](=[O:42])[CH3:41])=[CH:36][CH:35]=1.[C:43]([C:45]1[CH:46]=[C:47]([CH:50]=[CH:51][CH:52]=1)[CH:48]=O)#[N:44].C(=O)(O)[O-].[Na+]>ClCCl>[F:33][C:34]1[CH:39]=[CH:38][C:37]([C:40](=[O:42])[CH:41]=[CH:48][C:47]2[CH:46]=[C:45]([CH:52]=[CH:51][CH:50]=2)[C:43]#[N:44])=[CH:36][CH:35]=1

Participants

8

Reactant 6

HCID 98284'-FluoroacetophenoneHCID 62406Trifluoromethanesulfonic acidHCID 81531DiisopropylethylamineHCID 90670m-FormylbenzonitrileHCID 136618Dimethyl diphenylsilaneHCID 516892Sodium Bicarbonate

Product 1

HCID 54261868HCID 54261868, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Triflic acid (3.2 g, 21 mmol) is added portionwise to diphenyldimethylsilane (2.22 g, 10.5 mmol) in 20 mL of dichloromethane and stirred for 1 hour. After cooling to -78° C., diisopropylethylamine (1.42 g, 11 mmol) and 4'-fluoroacetophenone (1.38 g, 10 mmol) are added and the reaction mixture stirred for another hour before adding 3-cyanobenzaldehyde (1.0 g, 7.62 mmol). After the reaction mixture is stirred 18 hours, it is diluted with 100 mL of dichloromethane and stirred 1 hour with a saturated solution of sodium bicarbonate. The organic layer is separated, dried (MgSO4), concentrated and columned over SiO2 eluting with dichloromethane to provide 0.8 g of the title compound; mp 170°-172° C.

Workup

  1. stirringthe reaction mixture stirred for another hour
  2. stirringAfter the reaction mixture is stirred 18 hours
  3. customThe organic layer is separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1747380f47dd41559cd956c6854adc21
Source dataset
uspto-grants-1995_07
Patent number
US05430047

Reaction notes

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