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

반응식

HRID 335910 반응식
[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

참가 물질

4

반응물 2

HCID 673829092-bromo-3,5-difluoro-7-methoxy-9H-xanthen-9-oneHCID 178418332HCID 178418332, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-6d31548d0ce94dba926180b1dce661c8
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883782B2

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