Reaction #595371

Reaction equation

H2SO4

CO2

n-BuLi

diisopropylamine

1,4-difluoro-2-methoxybenzene

LDA

→

title compound

3,6-difluoro-2-methoxybenzoic acid

Solvents

diethyl ether

THF

THF

Conditions

Workup

1. 1
   Otherthe resulting precipitate was collected
2. 2
   Washwashed with H2O
3. 3
   Otherdried

Procedure

A solution of 1,4-difluoro-2-methoxybenzene (i-6a) (2.88 g, 20 mmol) in THF (5 mL) was added to a solution of LDA freshly prepared from n-BuLi (10M solution in hexane, 2.2 mL, 22 mmol) and diisopropylamine (2.28 g, 22.8 mmol) in THF (20 mL) at −60° C. After 30 min, a freshly prepared solution of CO2 in diethyl ether (20 mL) was quickly added. Then aq. H2SO4 was added, and the resulting precipitate was collected and washed with H2O, and dried to give the title compound (i-6b) as white crystals. LCMS (ESI) calc'd for C8H6F2O3 [M+H]+: 189. found: 189.

Source