Reacción #595371

ord-5aafd660425941529d5bb7699d4bd151

Ecuación de reacción

O=S(=O)(O)O
H2SO4
O=C=O
CO2
[Li][CH2]CCC
n-BuLi
CC(C)NC(C)C
diisopropylamine
COc1cc(F)ccc1F
1,4-difluoro-2-methoxybenzene
CC(C)[N-]C(C)C.[Li+]
LDA
COc1c(F)ccc(F)c1C(=O)O
title compound
COc1c(F)ccc(F)c1C(=O)O
3,6-difluoro-2-methoxybenzoic acid

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe resulting precipitate was collected
  2. 2
    Lavadowashed with H2O
  3. 3
    Otrodried

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09095583B2uspto-grants-2015_08