Sodium Hydroxide → 2-(4-Bromo-2-fluorophenyl)acetic acid

HRID 874474Notes

Reaction equation

HRID 874474 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](N)=[O:10])=[C:4]([F:12])[CH:3]=1.[OH-:13].[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:13])=[O:10])=[C:4]([F:12])[CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 66718910HCID 66718910, compound

Product 1

HCID 140537922-(4-Bromo-2-fluorophenyl)acetic acidYield 38%

Procedure

4-Bromo-2-fluoro-phenylacetamide (1.3 gm) was suspended in 100 ml of 30% NaOH, heating at reflux temperature for 24 hrs, cooled to room temperature, washed with DCM, and ethyl acetate. The aqueous layer was acidified with conc. HCl, extracted with ethyl acetate, evaporated; the residue was crystallized from isopropanol-water to give needle crystals (0.5 gm, 38%) H1-NMR INOVA-500 (DMSO d6) δ 3.619 (s, 2H), 7.316 (t, J=8.0 Hz, 1H), 7.379 (dd, J=8.0, 1.5 Hz, 1H), 7.516 (dd, J=8.0, 1.5 Hz, 1H), 12.555 (s, 1H).

Workup

  1. temperatureheating
  2. temperatureat reflux temperature for 24 hrs
  3. washwashed with DCM, and ethyl acetate
  4. extractionextracted with ethyl acetate
  5. customevaporated
  6. customthe residue was crystallized from isopropanol-water

Sources & evidence

ORD record
ord-46a8b9c61bf5467d94570ff4fc3bef22
Source dataset
uspto-grants-2015_03
Patent number
US08980890B2

Reaction notes

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