Boron tribromide → 5,6-Dihydroxy-7-nitro-1-benzofuran-2-carboxylic acid

HRID 1881196Notes

Reaction equation

C([O:3][C:4]([C:6]1[O:7][C:8]2[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([OH:18])[C:12]([O:19]C)=[CH:11][C:9]=2[CH:10]=1)=[O:5])C.B(Br)(Br)Br>ClCCl>[OH:19][C:12]1[C:13]([OH:18])=[C:14]([N+:15]([O-:17])=[O:16])[C:8]2[O:7][C:6]([C:4]([OH:5])=[O:3])=[CH:10][C:9]=2[CH:11]=1

Participants

Conditions

Temperature: -5 °C

Procedure

6-Hydroxy-5-methoxy-7-nitro-benzofuran-2-carboxylic acid ethyl ester (0.25 g) was dissolved to dichloromethane and cooled to −5° C. 1 M boron tribromide solution in dichloromethane (4.5 ml) was added and the mixture stirred at 0° C. for 24 hours. The mixture was poured in ice water and the dichloromethane layer separated. The water phase was extracted with ethyl acetate. The combined organic phases were dried with Na2SO4 and evaporated to dryness. The product was purified by reverse phase column chromatography using methanol (1%) in dichloromethane as an eluent.

Workup

customthe dichloromethane layer separated
extractionThe water phase was extracted with ethyl acetate
dry with materialThe combined organic phases were dried with Na2SO4
customevaporated to dryness
customThe product was purified by reverse phase column chromatography

Sources & evidence

ORD record: ord-d173e6c6e36148d18652128a5025d128
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318785B2

Reaction notes

Loading…