HCID 117599530, compound → HCID 117599550, compound

HRID 513243Notes

Reaction equation

HRID 513243 reaction equation
C[O:2][C:3](=O)[C:4]([C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[N+:19]([O-])=O)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5]>C(O)(=O)C.[Fe]>[Br:18][C:16]1[CH:17]=[C:12]2[C:13](=[CH:14][CH:15]=1)[NH:19][C:3](=[O:2])[C:4]2([CH3:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 117599530HCID 117599530, compound

Product 1

HCID 117599550HCID 117599550, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(5-Bromo-2-nitro-phenyl)-2-phenyl-propionic acid methyl ester (5.9 g, 16.25 mmol) and iron powder (3.64 g, 65 mmol) in acetic acid (100 mL) is heated to 70° C. and stirred for 3 hours. The acetic acid is removed in vacuo. The residue is diluted with satu. aq. NH4Cl solution and extracted with ethyl acetate (3×100 mL). The combined organic phase is washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue is recrystallized by ethyl acetate to give the desired product. Yield: 3.5 g (71%)

Workup

  1. customThe acetic acid is removed in vacuo
  2. additionThe residue is diluted with satu
  3. extractionaq. NH4Cl solution and extracted with ethyl acetate (3×100 mL)
  4. washThe combined organic phase is washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is recrystallized by ethyl acetate

Sources & evidence

ORD record
ord-02909d14069741c28faf2e40be2ec056
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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