Water → 4-Bromo-7-methoxybenzo[d][1,3]dioxole

HRID 1057940

반응식

HRID 1057940 반응식
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[C:4]([OH:5])[C:3]=1[OH:11].Br[CH2:13]Br.[F-].[K+].O>CN(C=O)C>[Br:1][C:2]1[C:3]2[O:11][CH2:13][O:5][C:4]=2[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 3024DibromomethaneHCID 522689Potassium FluorideHCID 37058743-Bromo-6-methoxybenzene-1,2-diol

생성물 1

HCID 111389764-Bromo-7-methoxybenzo[d][1,3]dioxole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

3-Bromo-6-methoxycatechol (23.4 g) was dissolved in DMF (150 ml), and dibromomethane (15.4 ml) and potassium fluoride (31.1 g) were added thereto, followed by heating at 110° C. for 6 hours with stirring. After being allowed to stand for cooling, water was added to the mixture followed by extraction with ether. The organic layer was washed with an aqueous solution of sodium hydroxide, with water, and with a saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/1) to give Compound IIbj-a (5.6 g, 40%) as a white solid.

후처리

  1. temperaturefor cooling
  2. extractionfollowed by extraction with ether
  3. washThe organic layer was washed with an aqueous solution of sodium hydroxide, with water
  4. dry with materialwith a saturated saline, and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/1)
  7. customto give Compound IIbj-a (5.6 g, 40%) as a white solid

출처 및 근거

ORD 기록
ord-35656327de7349fea2910113c9af3ce7
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514996B2

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