Water → Methyl 5-hydroxybenzofuran-2-carboxylate

A solution of 5-methoxybenzofuran-2-carboxylic acid methyl ester (5.15 g, 25 mmol) in anhydrous methylene chloride (15 ml) was cooled to −40° under nitrogen atmosphere. Boron tribromide in CH2Cl2 (27 ml of 1.0 M) was added over 1 h using a syringe pump. The reaction mixture was allowed to warm to room temperature. After 16 h, the reaction mixture was cooled in an ice bath and quenched with MeOH (15 ml). The reaction mixture was poured into brine (100 ml) and extracted with EtOAc. The organic extracts were dried over anhydrous MgSO4, and the solvent was removed on rotary evaporator. The residue was triturated with hexane and the yellow solid was filtered and dissolved in anhydrous MeOH (30 ml). The solution was cooled in an ice bath and thionyl chloride (1.9 ml, 26 mmol) was added dropwise. After 72 h, water (100 ml) was added and solid was collected. Purification of the crude product on a 300 cm3 silica gel in a 5×15 cm plug using EtOAc provided 5-hydroxy-benzofuran-2-carboxylic acid methyl ester (4.53 g).

1. temperaturethe reaction mixture was cooled in an ice bath
2. customquenched with MeOH (15 ml)
3. additionThe reaction mixture was poured into brine (100 ml)
4. extractionextracted with EtOAc
5. dry with materialThe organic extracts were dried over anhydrous MgSO4
6. customthe solvent was removed on rotary evaporator
7. customThe residue was triturated with hexane
8. filtrationthe yellow solid was filtered
9. dissolutiondissolved in anhydrous MeOH (30 ml)
10. temperatureThe solution was cooled in an ice bath
11. waitAfter 72 h
12. customsolid was collected
13. customPurification of the crude product on a 300 cm3 silica gel in a 5×15 cm plug

ORD record

ord-dd2a0cef49cc482488860135f71e8f23

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07482466B2