2,5-Difluoroaniline → Ethyl 2-(2,5-difluorophenylamino)-2-phenylacetate

HRID 1044045Notes

Reaction equation

HRID 1044045 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].Br[CH:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13].CCN(C(C)C)C(C)C>C(#N)C>[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH:4][CH:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 677752,5-DifluoroanilineHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 58556973Ethyl 2-(2,5-difluorophenylamino)-2-phenylacetateYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

2,5-Difluoroaniline (0.19 ml, 1.85 mmol), ethyl 2-bromo-2-phenylacetate (0.22 ml, 1.23 mmol), and DIPEA (0.32 ml, 1.85 mmol) were dissolved in acetonitrile (3 ml) and heated under MW irradiation at 100° C. for 6 hours and then at 110° C. for 4 hours. Acetonitrile was evaporated, and the crude product was purified by flash chromatography (Petroleum ether/EtOAc=97/3) to obtain intermediate I19 (240 mg, 67% yield).

Workup

  1. customAcetonitrile was evaporated
  2. customthe crude product was purified by flash chromatography (Petroleum ether/EtOAc=97/3)
  3. customto obtain intermediate I19 (240 mg, 67% yield)

Sources & evidence

ORD record
ord-d2df41d40465466eba022f33467865c4
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

Loading…