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

HRID 1501077

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HRID 1501077 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

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온도
90 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1b833afd42874844ae1646cec3f54531
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206128B2

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