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

HRID 1057940

反応式

HRID 1057940 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-35656327de7349fea2910113c9af3ce7
出典データセット
uspto-grants-2003_02
特許番号
US06514996B2

関連ノート

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