Sodium Carbonate → Tert-butyl 4-(benzofuran-2-yl)benzoate

HRID 1501077

反応式

HRID 1501077 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][CH:10]=2)O1.Br[C:24]1[O:25][C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[CH:28]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[O:25]1[C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[CH:28]=[C:24]1[C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[CH:20][CH:21]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27762642-Bromo-1-benzofuranHCID 43767661,1-Dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

生成物 1

HCID 89580933Tert-butyl 4-(benzofuran-2-yl)benzoate収率 67%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

To a solution of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.0 g, 3.3 mmol), 2-bromobenzofuran (0.64 g, 3.3 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.5 g, 0.4 mmol) in a mixed solution of 1,4-dioxane (20 mL) and water (2.0 mL) was added sodium carbonate (1.0 g, 7.2 mmol). The reaction mixture was stirred at 90° C. under nitrogen for 12 hours. After the reaction, it was allowed to cool to room temperature, and concentrated in vacuo, then diluted with ethyl acetate (100 mL), washed with water (100 mL). The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20) to give the pure product tert-butyl 4-(benzofuran-2-yl)benzoate as a white solid (0.65 g, 67%). 1H NMR (300 MHz, CDCl3): δ 8.06 (d, J=8.7 Hz, 2H), 7.90 (d, J=8.4 Hz, 2H), 7.62-7.53 (m, 2H), 7.32-7.25 (m, 2H), 7.14 (s, 1H), 1.62 (s, 9H).

後処理

  1. customAfter the reaction, it
  2. temperatureto cool to room temperature
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate (100 mL)
  5. washwashed with water (100 mL)
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20)

出典と根拠

ORDレコード
ord-1b833afd42874844ae1646cec3f54531
出典データセット
uspto-grants-2015_12
特許番号
US09206128B2

関連ノート

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