(2-Bromo-4-nitrophenyl)acetic acid → HCID 12404389, compound

HRID 2173392Notes

Reaction equation

HRID 2173392 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([OH:14])=[O:13]>[OH-].[NH4+].O>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:11][C:12]([OH:14])=[O:13])=[C:2]([Br:1])[CH:7]=1

Participants

4

Reactant 1

HCID 12404388(2-Bromo-4-nitrophenyl)acetic acid

Product 1

HCID 12404389HCID 12404389, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A solution of (2-bromo-4-nitrophenyl)acetic acid (500 mg, 2 mmol) in 11 mL of concentrated ammonium hydroxide was added a solution of FeSO4.7H2O (3.4 g, 12 mmol) in 11 mL of water over 5 minutes, and then the mixture was heated to reflux for 1 hour. Cooled to ambient temperature, filtered off solids and the filtrate was adjusted to pH to 5 with 2N HCl. Extracted with EtOAc and combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated to get (4-amino-2-bromophenyl)acetic acid. 1H-NMR (300 MHz, CDCl3) δ ppm 7.01 (d, J=8.0 Hz, 1H), 6.92 (d, J=2.0 Hz, 1H), 6.62 (dd, J=2.5 Hz, 1H), 3.61 (s, 2H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationfiltered off solids
  4. extractionExtracted with EtOAc
  5. washwere washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-953dc95a5762439fb61d8f5fe8a545d2
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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