2,4-Difluoronitrobenzene → Glycine, N-(5-fluoro-2-nitrophenyl)-, ethyl ester

HRID 1899917Notes

Reaction equation

HRID 1899917 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Cl.[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH2:18])[CH3:14].C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:13]([O:15][C:16](=[O:19])[CH2:17][NH:18][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[CH3:14]

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 10331949Glycine, N-(5-fluoro-2-nitrophenyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2,4-difluoronitrobenzene (VII, 19.20 g), glycine ethyl ester hydrochloride (XII, 16.52 g), and acetonitrile (50 ml) is added diisopropylethylamine (42 ml). A mild exotherm ensues. The reaction is stirred (without cooling) for two hours. The acetonitrile is removed under reduced pressure and the residue is partitioned between dichloromethane and water. The organic layers are dried over sodium sulfate and concentrated to give the produce as a solid (single spot by TLC), mp 194°-195°; NMR (CDCl3) 1.33, 4.05, 4.30, 6.35, 6.45, 8.26 and 8.56 β.

Workup

  1. temperature(without cooling) for two hours
  2. customThe acetonitrile is removed under reduced pressure
  3. customthe residue is partitioned between dichloromethane and water
  4. dry with materialThe organic layers are dried over sodium sulfate
  5. concentrationconcentrated
  6. customto give the
  7. customproduce as a solid (single spot by TLC), mp 194°-195°

Sources & evidence

ORD record
ord-ff109cd5948b4b9f874dcb48149134f3
Source dataset
uspto-grants-1996_11
Patent number
US05574038

Reaction notes

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