Hydrochloric Acid → 4-Bromo-2-nitrophenylacetic Acid

HRID 1387412Notes

Reaction equation

HRID 1387412 reaction equation
[OH:1]O.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:15])C(O)=O)=[C:6]([N+:16]([O-:18])=[O:17])[CH:5]=1.[OH-].[Na+].Cl>O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:15])=[O:1])=[C:6]([N+:16]([O-:18])=[O:17])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 271544HCID 271544, compound

Product 1

HCID 2715514-Bromo-2-nitrophenylacetic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 30% hydrogen peroxide solution (4.95 mL, 0.04 mol) was added dropwise to a solution of 4-bromo-2-nitrophenylpyruvic acid (0.04 mol) and sodium hydroxide (5.3 g 0.1 mol) in water (175 mL) stirring at 0° C. The reaction solution was stirred for 1 h at 5° C. and then acidified with dilute HCl. The yellow precipitate was filtered and the crude product recrystallized from hexane and ethyl acetate to yield 8.4 g (75%) as a light beige solid; 1H-NMR (DMSO-d6): δ12.67 (br s, 1H), 8.28 (d, J=2.0 Hz), 7.97 (dd, 1H, J=9.0 Hz, 2.0 Hz), 7.55 (d, 1H, J=8.0 Hz 4.00 (s, 3H). MS (−ve) m/z: 259 (M−H).

Workup

  1. stirringThe reaction solution was stirred for 1 h at 5° C.
  2. filtrationThe yellow precipitate was filtered
  3. customthe crude product recrystallized from hexane and ethyl acetate
  4. customto yield 8.4 g (75%) as a light beige solid

Sources & evidence

ORD record
ord-d0e1c2318e49401697926c45ae0ee165
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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