Benzofuran → Benzo[b]furan-2-yl-(3-bromo-6-fluoro-2-methoxy-phenyl)-methanol

HRID 503180ノート

反応式

HRID 503180 の反応式
C([Li])CCC.[CH:6]1[CH:11]=[C:10]2[CH:12]=[CH:13][O:14][C:9]2=[CH:8][CH:7]=1.[Br:15][C:16]1[C:17]([O:25][CH3:26])=[C:18]([C:21]([F:24])=[CH:22][CH:23]=1)[CH:19]=[O:20].[Cl-].[NH4+]>CCCCCC.O1CCCC1.O>[O:14]1[C:13]([CH:19]([C:18]2[C:21]([F:24])=[CH:22][CH:23]=[C:16]([Br:15])[C:17]=2[O:25][CH3:26])[OH:20])=[CH:12][C:10]2[CH:11]=[CH:6][CH:7]=[CH:8][C:9]1=2

参加物

8

反応物 4

HCID 9223BenzofuranHCID 25517Ammonium ChlorideHCID 222610733-Bromo-6-fluoro-2-methoxybenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 22261032Benzo[b]furan-2-yl-(3-bromo-6-fluoro-2-methoxy-phenyl)-methanol収率 66.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

In an atmosphere of nitrogen gas, 3.56 ml of a 2.66 M solution of n-butyllithium in hexane was added to a solution of 1.12 g of 2,3-benzofuran in 10 ml tetrahydrofuran at −78° C. After stirring at the same temperature for 10 minutes, the mixture was stirred under ice-cooling for 15 minutes and was then stirred at −78° C. for 8 minutes. Then, a solution of 2 g of 3-bromo-6-fluoro-2-methoxy-benzaldehyde in 3.5 ml tetrahydrofuran was added dropwise at the same temperature. After stirring at the same temperature for 30 minutes, saturated aqueous ammonium chloride solution was added at the same temperature. Water was added at room temperature and the mixture was extracted with diethyl ether for two times. The organic layer was sequentially washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography, to give 2 g of the title compound as a yellow oil.

後処理

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 15 minutes
  3. stirringwas then stirred at −78° C. for 8 minutes
  4. stirringAfter stirring at the same temperature for 30 minutes
  5. extractionthe mixture was extracted with diethyl ether for two times
  6. washThe organic layer was sequentially washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe crude product was purified
  10. customseparated by silica gel column chromatography

出典と根拠

ORDレコード
ord-e09f7bd89594421ab07e77fa7d155256
出典データセット
uspto-grants-2010_08
特許番号
US07776890B2

反応ノート

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