2-Chloro-6-methoxybenzoic acid → HCID 28945846, compound

To a stirred solution of 2-chloro-6-(methyloxy)benzoic acid (0.252 g, 1.35 mmol, Arkpharminc) in dry THF (15 ml) at ambient temperature under nitrogen was added 1 M borane tetrahydrofuran complex (4.1 ml of solution in THF, 4.1 mmol, Aldrich) dropwise. The solution was then heated at reflux for 24 h and allowed to cool. The reaction mixture was quenched by the dropwise addition of methanol (4 ml), then heated at reflux for 30 min and allowed to cool. The solvent was removed in vacuo and the residue was partitioned between dilute aqueous ˜1M aqueous HCl and chloroform, the aqueous phase being extracted with more chloroform and the chloroform solutions being filtered through a phase separator. The combined chloroform solutions were evaporated in vacuo to give the title compound as a pale yellow solid (0.225 g); LCMS: (System 4) MH+=173, tRET=1.86 min.

1. temperatureThe solution was then heated
2. temperatureat reflux for 24 h
3. temperatureto cool
4. customThe reaction mixture was quenched by the dropwise addition of methanol (4 ml)
5. temperatureheated
6. temperatureat reflux for 30 min
7. temperatureto cool
8. customThe solvent was removed in vacuo
9. customthe residue was partitioned between dilute aqueous ˜1M aqueous HCl and chloroform
10. extractionthe aqueous phase being extracted with more chloroform
11. filtrationthe chloroform solutions being filtered through a phase separator
12. customThe combined chloroform solutions were evaporated in vacuo

ORD record

ord-c452d5cc2b3c4ecd845ff007b67e9700

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399436B2