Water → Methyl 4-bromofuran-2-carboxylate

HRID 1845477

반응식

HRID 1845477 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 4135083Methyl 4,5-Dibromo-2-furancarboxylateHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 12239443Methyl 4-bromofuran-2-carboxylate수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b8129193ff50437ca04d79cc8a631263
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946278B2

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