7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one → 7-bromo-4-fluoro-2-methoxy-9-methyl-9H-xanthen-9-ol

HRID 335915

反応式

HRID 335915 の反応式
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:19])=[CH:9][C:10]([O:17][CH3:18])=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.[CH3:20][Mg]Cl>C1COCC1>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:19])=[CH:9][C:10]([O:17][CH3:18])=[CH:11][C:12]=3[C:13]2([CH3:20])[OH:16])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 574756397-bromo-4-fluoro-2-methoxy-9H-xanthen-9-oneHCID 178418332HCID 178418332、化合物

生成物 1

HCID 673829217-bromo-4-fluoro-2-methoxy-9-methyl-9H-xanthen-9-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-30 °C

実験手順

7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one (22 g, 68.1 mmol) was dissolved in 300 ml of THF and cooled to −30° C. in a dry ice ACN bath. Methylmagnesium chloride (34.0 mL, 102 mmol) (3M in THF) was added to the slurry maintaining temperature less than −15° C. The solution was allowed to warm to RT (undissolved solids went into solution), then quenched with saturated NH4Cl (250 mL). The aqueous layer was extracted with EtOAc (3×200 mL) and the combined organic layers were washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated to afford 7-bromo-4-fluoro-2-methoxy-9-methyl-9H-xanthen-9-ol as a brown liquid that was used without further purification.

後処理

  1. temperaturemaintaining temperature less than −15° C
  2. temperatureto warm to RT (undissolved solids went into solution)
  3. customquenched with saturated NH4Cl (250 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (3×200 mL)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-6a8d8e9f9362467796036fcc222f81eb
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

関連ノート

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