Hydrochloric Acid → Methyl 5-fluoro-3-benzofurancarboxylate

HRID 1936612Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]([OH:12])=[O:11])[C:6]=2[CH:13]=1.Cl.[CH3:15]O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]([O:12][CH3:15])=[O:11])[C:6]=2[CH:13]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 181843085-fluoro-1-benzofuran-3-carboxylic acid

Product 1

HCID 18184300Methyl 5-fluoro-3-benzofurancarboxylate

Procedure

A solution of 5-fluorobenzofuran-3-carboxylic acid (56 g) and saturated etheral solution of hydrochloric gas (300 mL) in methanol (600 mL) was stirred for 16 h at room temperature. Further etheral HCl was added (300 mL) followed by stirring for 24 h. Concentration in vacuo gave a dark crystalline material, methyl 5-fluorobenzofuran-3-carboxylate (58 g).

Workup

concentrationConcentration in vacuo

Sources & evidence

ORD record: ord-5c975471851546a18be6c5a3dd7c5540
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391882B1

Reaction notes

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