Hydroquinone → N-(2-Fluorophenyl)-2-(4-hydroxyphenoxy)-N-methylpropanamide

HRID 1018900Notes

Reaction equation

HRID 1018900 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:14])[C:9](=[O:13])[CH:10](Br)[CH3:11].[C:15]1([CH:22]=[CH:21][C:19]([OH:20])=[CH:18][CH:17]=1)[OH:16].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:14])[C:9](=[O:13])[CH:10]([O:16][C:15]1[CH:22]=[CH:21][C:19]([OH:20])=[CH:18][CH:17]=1)[CH3:11]

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 18183268HCID 18183268, compound

Product 1

HCID 18183267N-(2-Fluorophenyl)-2-(4-hydroxyphenoxy)-N-methylpropanamideYield 86.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

N-(2-fluorophenyl)-N-methyl-2-bromopropionamide(18.2 g, 0.07 mol), hydroquinone(7 g, 0.064 mol), potassium carbonate(10.54 g, 0.076 mol) and tetra-n-butylammonium bromide(1 g) were dissolved in 350 ml of acetonitrile and heated at reflux for 6 hours. The reaction mixture was cooled to room temperature and solid remained during the reaction was filtered out. The filtrate was concentrated under reduced pressure and the crude product was purified by column chromatography(eluent: ethyl acetate/n-hexane=1/2) to afford 16 g of the target product.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. filtrationwas filtered out
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe crude product was purified by column chromatography(eluent

Sources & evidence

ORD record
ord-027d44da8d9f412483f59f282b3e1529
Source dataset
uspto-grants-2002_11
Patent number
US06486098B1

Reaction notes

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