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

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

Reactant 2

HCID 14798Sodium Hydroxide

HCID 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

temperatureheating
temperatureat reflux temperature for 24 hrs
washwashed with DCM, and ethyl acetate
extractionextracted with ethyl acetate
customevaporated
customthe residue was crystallized from isopropanol-water

Sources & evidence

ORD record: ord-46a8b9c61bf5467d94570ff4fc3bef22
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980890B2

Reaction notes

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