Potassium Fluoride → HCID 86672768, compound

HRID 1754982Notes

Reaction equation

HRID 1754982 reaction equation
[F-:1].[K+].CS(O[CH2:8][CH2:9][O:10][CH2:11][CH2:12][N:13]([C:23](=[O:25])[CH3:24])[C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([Br:21])=[C:16]([CH3:22])[CH:15]=1)(=O)=O>C(OCC)(=O)C>[Br:21][C:17]1[C:18]([CH3:20])=[CH:19][C:14]([N:13]([CH2:12][CH2:11][O:10][CH2:9][CH2:8][F:1])[C:23](=[O:25])[CH3:24])=[CH:15][C:16]=1[CH3:22]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 86672769HCID 86672769, compound

Product 1

HCID 86672768HCID 86672768, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium fluoride (180 mg, 3.11 mmol) was added to a solution of 2-[2-[acetyl-(4-bromo-3,5-dimethyl-phenyl)amino]ethoxy]ethyl methanesulfonate (254 mg, 0.622 mmol) in PEG200 (2 ml), and the mixture was irradiated with microwaves at 100° C. for 10 minutes. The reaction solution was diluted with ethyl acetate, and the organic layer was sequentially washed with water and saturated brine and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give N-(4-bromo-3,5-dimethyl-phenyl)-N-[2-(2-fluoroethoxy)ethyl]acetamide (144 mg, 70%).

Workup

  1. customthe mixture was irradiated with microwaves at 100° C. for 10 minutes
  2. washthe organic layer was sequentially washed with water and saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ae8c069519f74c4fbe1ad74b8df51af9
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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