Potassium Carbonate → 3-{2-[3-(3,4-Dichloro-benzyloxy)-phenyl]-2-oxo-ethoxy}-4-fluoro-benzonitrile

HRID 708610Notes

Reaction equation

HRID 708610 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][CH:18]=[C:17]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=2)[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:17]1[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][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 207769814-Fluoro-3-hydroxybenzonitrileHCID 583275612-Bromo-1-[3-(3,4-dichloro-benzyloxy)-phenyl]-ethanone

Product 1

HCID 583271093-{2-[3-(3,4-Dichloro-benzyloxy)-phenyl]-2-oxo-ethoxy}-4-fluoro-benzonitrileYield 87.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Fluoro-3-hydroxy-benzonitrile (7.3 g), 2-bromo-1-[3-(3,4-dichloro-benzyloxy)-phenyl]-ethanone (22 g), and potassium carbonate (24.3 g) were suspended together in 400 mL acetone with stirring. The mixture continued to stir for 8 hours, then was concentrated to dryness. The solid residue was taken up in 150 mL diethyl ether and 150 mL water and stirred 2 hours. The solid product was collected by filtration and washed with 100 mL diethyl ether two times and dried in vacuum, 20 g of desired product was obtained. 1H NMR (400 MHz, DMSO-d6): 7.80-7.85 (m, 1H), 7.77 (d, 1H), 7.67 (m, 1H), 7.57-7.64 (m, 2H), 7.44-7.54 (m, 4H), 7.34-7.36 (m, 1H), 5.77 (s, 2H), 5.21 (s, 2H).

Workup

  1. stirringto stir for 8 hours
  2. concentrationwas concentrated to dryness
  3. stirring150 mL water and stirred 2 hours
  4. filtrationThe solid product was collected by filtration
  5. washwashed with 100 mL diethyl ether two times
  6. customdried in vacuum

Sources & evidence

ORD record
ord-0646681d8ca84a4ca61b33d2cc7d1427
Source dataset
uspto-grants-2015_11
Patent number
US09175003B2

Reaction notes

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