Water → Methyl 4-bromofuran-2-carboxylate

Temperatur

25 °C

To a solution of methyl 4,5-dibromo-2-furancarboxylate (1 g, 3.52 mmol) in tetrahydrofuran (14.1 ml) at −40° C. was added isopropylmagnesium chloride (1.85 ml, 3.70 mmol). After 2 h, H2O (3.52 ml) was added and the solution warmed to 25° C. The reaction mixture was then partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and purified by column chromatography (3% EtOAc in hexanes) affording methyl 4-bromo-2-furancarboxylate (470 mg, 2.04 mmol, 58% yield) as a white solid: LCMS (ES) m/e 204, 206 (M, M+2)+.

1. customThe reaction mixture was then partitioned between H2O-DCM
2. washthe aqueous phase was washed several times with DCM
3. dry with materialThe combined organic fractions were dried over Na2SO4
4. concentrationconcentrated
5. custompurified by column chromatography (3% EtOAc in hexanes)

ORD-Eintrag

ord-b8129193ff50437ca04d79cc8a631263

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08946278B2