Acetic Acid → 2-Fluoro-5-hydroxybenzoic acid

HRID 714116Notes

Reaction equation

HRID 714116 reaction equation
[F:1][C:2]1C=[CH:8][C:7]([O:10]C)=[CH:6][C:3]=1C#N.[C:12]([OH:15])(=[O:14])[CH3:13]>Br.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:6][C:7]([OH:10])=[CH:8][C:13]=1[C:12]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 27745462-Fluoro-5-methoxybenzonitrile

Product 1

HCID 27744802-Fluoro-5-hydroxybenzoic acid

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Fluoro-5-methoxybenzonitrile (3d, purchased from Alfa Aesar) (5 g, 33 mmol) was dissolved in hydrobromic acid (50 mL) and glacial acetic acid (30 mL), refluxed for 28 hours at 140° C., and then the reaction mixture was diluted with 100 mL ethyl acetate. The reaction mixture was then washed with 50 mL water and saturated sodium chloride solution successively for three times. The organic layers were combined and concentrated to give a crude product of 2-fluoro-5-hydroxybenzoic acid (3e), 2.88 g white solid (yield 56%). 1H NMR (600 MHz, DMSO-d6) δ 7.19-7.17 (m, 1H), 7.08-7.04 (m, 1H), 6.95-6.92 (m, 1H); ESI-MS m/z: calculated for 156.02. found 154.91 [M−H]+.

Workup

  1. washThe reaction mixture was then washed with 50 mL water and saturated sodium chloride solution successively for three times
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-033fb64703a748a7b4d1e111c3f5a333
Source dataset
uspto-grants-2015_11
Patent number
US09187430B2

Reaction notes

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