Methyl 4,5-Dibromo-2-furancarboxylate → Methyl 4-bromo-5-methylfuran-2-carboxylate

HRID 1845697

反応式

HRID 1845697 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1Br.Cl[Zn][CH3:14]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1[CH3:14]

参加物

5

反応物 2

HCID 4135083Methyl 4,5-Dibromo-2-furancarboxylateHCID 178477798HCID 178477798、化合物

生成物 1

HCID 604544Methyl 4-bromo-5-methylfuran-2-carboxylate収率 72%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 4,5-dibromo-2-furancarboxylate (4.5 g, 15.85 mmol) and BIS(TRIPHENYLPHOSPHINE)PALLADIUM(II) CHLORIDE (0.38 g, 0.541 mmol) in THF (100 mL) at RT was added chloro(methyl)zinc (15 mL, 30 mmol) dropwise. After stirring for 10 h, the reaction was quenched with NH4Cl (sat'd) (50 mL). The mixture was extracted with EtOAc (50 mL×3), and the collected organic layers were dried over MgSO4. Solvent was removed under vacuum and the resulting residue was purified via column chromatography (silica, EtOAc/Hex 10-20%) to give the title compound (2.5 g, 72%) as a white solid: LC-MS (ES) m/z 220 (M+H)+.

後処理

  1. customthe reaction was quenched with NH4Cl (sat'd) (50 mL)
  2. extractionThe mixture was extracted with EtOAc (50 mL×3)
  3. dry with materialthe collected organic layers were dried over MgSO4
  4. customSolvent was removed under vacuum
  5. customthe resulting residue was purified via column chromatography (silica, EtOAc/Hex 10-20%)

出典と根拠

ORDレコード
ord-0cf7215562f1448a868bae8bfbfd8b32
出典データセット
uspto-grants-2015_02
特許番号
US08946278B2

関連ノート

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