Reaction #491516

Reaction equation

2-fluoro-4-hydroxybenzoic acid

sulfuric acid

MeOH

→

T7.1

Yield 85.0%

Methyl 2-fluoro-4-hydroxybenzoate

Yield 85.0%

Conditions

Workup

1. 1
   Otherthe solvent was removed
2. 2
   workup.ADDITIONthe residue was diluted with diethyl ether
3. 3
   WashThe organic phase was washed carefully two times with saturated aqueous NaHCO3
4. 4
   Dryingonce with brine, and then dried over anhydrous sodium sulfate
5. 5
   FiltrationAfter filtration
6. 6
   Otherthe organic solvent was removed in vacuo

Procedure

To a round bottom containing 2-fluoro-4-hydroxybenzoic acid (Commercially available from TCI America) (5.34 g, 34.19 mmol) was added a cold solution of MeOH (50 mL) and sulfuric acid (2.0 mL). The mixture was heated to 80° C. and monitored with TLC. After 20.5 hours, the solvent was removed and the residue was diluted with diethyl ether. The organic phase was washed carefully two times with saturated aqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to yield T7.1 as a white solid (5.82, 85% yield). 1H NMR (400 MHz, DMSO-d6) 10.79 (1H, s), 7.75 (1H, t, J=8.8 Hz), 6.69 (1H, dd, J=8.6, 2.3 Hz), 6.62 (1H, dd, J=13.1, 2.2 Hz), 3.78 (3H, s).

Source