Potassium Carbonate → 3-(2-(4-((3,4-Dichlorobenzyl)oxy)phenyl)-2-oxoethoxy)-4-fluorobenzonitrile

HRID 879676Notes

Reaction equation

HRID 879676 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[OH:10].Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[Cl:29])[CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH2:12][O:10][C:3]2[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=2[F:1])[C:6]#[N:7])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 207769814-Fluoro-3-hydroxybenzonitrileHCID 583275742-Bromo-1-[4-(3,4-dichloro-benzyloxy)-phenyl]-ethanone

Product 1

HCID 583271623-(2-(4-((3,4-Dichlorobenzyl)oxy)phenyl)-2-oxoethoxy)-4-fluorobenzonitrileYield 102%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Fluoro-3-hydroxy-benzonitrile (15 g), 2-bromo-1-[4-(3,4-dichloro-benzyloxy)-phenyl]-ethanone (45 g), and potassium carbonate 45 g) were suspended together in 630 mL acetone with stirring. The mixture continued to stir for 18 hours, then was concentrated to dryness. The solid residue was taken up in 500 mL diethyl ether and stirred 1.5 h, then 1 L water was added and stirred vigorously an additional 3 hours. The solid product was collected by filtration and washed with 200 mL diethyl ether three times. It was then dissolved in THF, filtered to remove any remaining inorganic salt, and evaporated again to dryness. After drying under vacuum 18 h, 48 g of desired product was obtained (quantitative). 1H NMR (400 MHz, DMSO-d6): 7.97 (d, 2H), 7.66 (d, 1H), 7.45 (m, 2H), 7.46 (m, 3H), 7.16 (d, 2H), 5.72 (s, 2H), 5.25 (s, 2H).

Workup

  1. stirringto stir for 18 hours
  2. concentrationwas concentrated to dryness
  3. stirringstirred 1.5 h
  4. addition1 L water was added
  5. stirringstirred vigorously an additional 3 hours
  6. filtrationThe solid product was collected by filtration
  7. washwashed with 200 mL diethyl ether three times
  8. dissolutionIt was then dissolved in THF
  9. filtrationfiltered
  10. customto remove any remaining inorganic salt
  11. customevaporated again to dryness
  12. customAfter drying under vacuum 18 h

Sources & evidence

ORD record
ord-68776862ee564d849cd2e3a72833272a
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Reaction notes

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