N-bromobutanimide → Methyl 5-bromo-2-methylfuran-3-carboxylate

HRID 383592

반응식

HRID 383592 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][O:7][C:6]=1[CH3:10])=[O:4].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([Br:18])[O:7][C:6]=1[CH3:10])=[O:4]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 80237Methyl 2-methylfuran-3-carboxylate

생성물 1

HCID 15534190Methyl 5-bromo-2-methylfuran-3-carboxylate수율 80.4%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6212Chloroform용매

실험 절차

(The following reaction is done under exclusion of light.) Dissolve 2-Methyl-furan-3-carboxylic acid methyl ester (22) (2.00 mL, 15.9 mmol) in chloroform (11 mL) and glacial acetic acid (11 mL) and add NBS (3.85 g, 21.6 mmol) portionwise in between a period of 75 min. Stir the reaction suspension for additional 16 h at rt. Add water to the reaction mixture and extract the aqu. layer with DCM (2 times), wash the combined organic layer with 2M aqu. NaOH, water and brine and dry it with Na2SO4 to obtain 5-Bromo-2-methyl-furan-3-carboxylic acid methyl ester (23) (2.80 g, 80%) as a red brown oil. No further purification. 1H NMR (400 MHz, CDCl3): 2.54 (s, 3H); 3.80 (s, 3H); 6.53 (s, 1H).

후처리

  1. custom(The following reaction
  2. extractionAdd water to the reaction mixture and extract the aqu
  3. washlayer with DCM (2 times), wash the combined organic layer with 2M aqu
  4. dry with materialNaOH, water and brine and dry it with Na2SO4

출처 및 근거

ORD 기록
ord-2439eb522eb44d7eaf14b632d326e6f7
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367677B2

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