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

HRID 383592

反応式

HRID 383592 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 15534190Methyl 5-bromo-2-methylfuran-3-carboxylate収率 80.4%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-2439eb522eb44d7eaf14b632d326e6f7
出典データセット
uspto-grants-2013_02
特許番号
US08367677B2

関連ノート

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