Water → Methyl 4-bromofuran-2-carboxylate

HRID 1845477

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1Br.C([Mg]Cl)(C)C.O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][CH:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

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)+.

Workup

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

Sources & evidence

ORD record: ord-b8129193ff50437ca04d79cc8a631263
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946278B2

Linked notes

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