4-Fluoroaniline → HCID 58556899, compound

HRID 453680Notes

Reaction equation

HRID 453680 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br[CH:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(#N)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 58556899HCID 58556899, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluoroaniline (2.38 ml, 24.8 mmol) was added to a solution of ethyl 2-bromo-2-phenylacetate (4.34 ml, 24.8 mmol) in acetonitrile (50 ml). The reaction was heated under microwave irradiation at 100° C. for 30 minutes. Acetonitrile was evaporated, the residue was taken up with EtOAc and washed with 1N NaHCO3, 1N HCl and brine (100 ml). The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography (Petroleum ether/EtOAc=99/1 to 8/2) to afford ethyl 2-(4-fluorophenylamino)-2-phenylacetate (4.90 g, 72.3% yield).

Workup

  1. customAcetonitrile was evaporated
  2. washwashed with 1N NaHCO3, 1N HCl and brine (100 ml)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography (Petroleum ether/EtOAc=99/1 to 8/2)

Sources & evidence

ORD record
ord-18ada64b6fc8483792c1997cd18c704e
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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