Potassium Carbonate → 4-Bromo-3,5-dimethylphenyl 3-(4-nitrophenyl)propiolate

HRID 1483190ノート

反応式

HRID 1483190 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([Br:29])=[C:24]([CH3:30])[CH:23]=1)(=[O:20])[C:18]#[CH:19]>C1COCC1.[Cu]I>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:19]#[C:18][C:17]([O:21][C:22]2[CH:23]=[C:24]([CH3:30])[C:25]([Br:29])=[C:26]([CH3:28])[CH:27]=2)=[O:20])=[CH:3][CH:4]=1)([O-:10])=[O:9]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 124951-Iodo-4-nitrobenzeneHCID 725452334-Bromo-3,5-dimethylphenyl propiolate

生成物 1

HCID 725454764-Bromo-3,5-dimethylphenyl 3-(4-nitrophenyl)propiolate収率 74%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
65 °C

実験手順

1-Iodo-4-nitrobenzene (550 mg, 2.17 mmol) in THF (4 mL) was degassed under reduced pressure at −78° C., and then nitrogen gas was introduced. To the solution was added K2CO3 (552 mg, 298.6 mmol), CuI (30 mg, 0.16 mmol) and PdCl2(Ph3P)2 (14 mg, 0.020 mmol), and the mixture was stirred at 65° C. 4-bromo-3,5-dimethylphenyl propiolate (6-1) (506 mg, 2.03 mmol) in THF (2.5 mL) was added by syringe pump over a period of 6 h. After being cooled to room temperature, the mixture was filtered and washed with EtOAc. The filtrate was concentrated and purified by silica gel column chromatography to give the title compound 7-1 (551 mg, 74% yield) as a brown solid.

後処理

  1. additionnitrogen gas was introduced
  2. temperatureAfter being cooled to room temperature
  3. filtrationthe mixture was filtered
  4. washwashed with EtOAc
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-cb9e5fa46bd34dd29ce6afa7a9084312
出典データセット
uspto-grants-2016_08
特許番号
US09416121B2

反応ノート

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