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

HRID 76993

Reaction equation

HRID 76993 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>[CH2:15]([O:14][C:12](=[O:13])[CH:11]([NH:4][C:3]1[CH:5]=[C:6]([F:9])[CH:7]=[CH:8][C:2]=1[F:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16]

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) are 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 is evaporated and the crude is purified by flash chromatography (Petroleum ether/EtOAc=97/3) to obtain intermediate I104 as a white solid (240 mg, 67% yield).

Workup

  1. customAcetonitrile is evaporated
  2. customthe crude is purified by flash chromatography (Petroleum ether/EtOAc=97/3)

Sources & evidence

ORD record
ord-7adf7ece2fe84b79a4fb7b0fe2f787f8
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

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