2-bromo-3,5-difluoro-7-methoxy-9H-xanthen-9-one → 2-bromo-3,5-difluoro-7-methoxy-9-methyl-9H-xanthen-9-ol

HRID 335910

反応式

HRID 335910 の反応式
[Br:1][C:2]1[C:15]([F:16])=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:18][CH3:19])=[CH:9][C:10]=3[F:17])[C:5](=[O:20])[C:4]=2[CH:3]=1.[CH3:21][Mg]Cl>C1COCC1>[Br:1][C:2]1[C:15]([F:16])=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:18][CH3:19])=[CH:9][C:10]=3[F:17])[C:5]([CH3:21])([OH:20])[C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 673829092-bromo-3,5-difluoro-7-methoxy-9H-xanthen-9-oneHCID 178418332HCID 178418332、化合物

生成物 1

HCID 673835462-bromo-3,5-difluoro-7-methoxy-9-methyl-9H-xanthen-9-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A mixture of 2-bromo-3,5-difluoro-7-methoxy-9H-xanthen-9-one (40 g, 117 mmol) and THF (300 mL) was cooled to 0° C. and treated with methylmagnesium chloride (58.6 mL, 176 mmol) (3M in THF). After stirring at this temperature for 20 minutes, the reaction was quenched by the addition of sataturated NH4Cl (500 mL). Brine was added and the mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo to afford crude 2-bromo-3,5-difluoro-7-methoxy-9-methyl-9H-xanthen-9-ol as a brown solid that was carried on without further purification. MS m/z=339.0 [M+1−H2O].

後処理

  1. customthe reaction was quenched by the addition of sataturated NH4Cl (500 mL)
  2. additionBrine was added
  3. extractionthe mixture was extracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6d31548d0ce94dba926180b1dce661c8
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

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