Triethylamine → 4-(4-(4-Chlorophenyl)-2-oxo-2,5-dihydrofuran-3-yl)benzonitrile

HRID 1661097Notes

Reaction equation

HRID 1661097 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)#[N:2].CC(C)([O-])C.[K+].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=O.CCN(CC)CC>CN(C=O)C.O.CCO>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:21]2[CH2:20][O:11][C:10](=[O:12])[C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 68303p-Chlorophenacyl bromideHCID 795874-Cyanophenylacetic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 671287984-(4-(4-Chlorophenyl)-2-oxo-2,5-dihydrofuran-3-yl)benzonitrileYield 91%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred and cooled (−15° to −10° C.) solution of 2-(4-cyanophenyl)acetic acid (35 g, 217.18 mmol) in DMF (250 mL) was added potassium t-butoxide (95%, 25.66 g, 217.22 mmol) under argon in small portions keeping the temperature below −10° C. After the addition was complete a solution of 2-bromo-1-(4-chlorophenyl)ethanone (50.71 g, 217.18 mmol) in DMF (75 mL) was added slowly over 30 min. The reaction mixture was stirred for 1 hr keeping the temperature between −10° to 0° C. Et3N (12.0 mL, 86.1 mmol) was added at 0° C. and the reaction mixture was allowed to warm to room temperature over 1.5 hr. Then EtOH (70 mL) was added at room temperature and the reaction mixture was stirred for 10 min. The reaction mixture was cooled in an ice bath and water (300 mL) was added slowly. The light green precipitate formed was collected by filtration, washed thoroughly with water followed by hexanes. The solid thus obtained was dried in a vacuum oven overnight at 50° C. to obtain 4-(4-(4-chlorophenyl)-2-oxo-2,5-dihydrofuran-3-yl)benzonitrile (58.2 g, 91% yield) as a light green solid.

Workup

  1. customthe temperature below −10° C
  2. additionAfter the addition
  3. additionwas added slowly over 30 min
  4. stirringThe reaction mixture was stirred for 1 hr
  5. custombetween −10° to 0° C
  6. stirringthe reaction mixture was stirred for 10 min
  7. temperatureThe reaction mixture was cooled in an ice bath
  8. customThe light green precipitate formed
  9. filtrationwas collected by filtration
  10. washwashed thoroughly with water
  11. customThe solid thus obtained
  12. customwas dried in a vacuum oven overnight at 50° C.

Sources & evidence

ORD record
ord-06a42a979817431182cecc6074b2bc05
Source dataset
uspto-grants-2011_10
Patent number
US08030306B2

Reaction notes

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