Nitrogen → 2-Bromo-4'-tert-butylbiphenyl

HRID 1499346

반응식

HRID 1499346 반응식
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1B(O)O.Br[C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=1.N#N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC.O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=1

참가 물질

9

반응물 5

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 775951-Bromo-4-tert-butylbenzeneHCID 2773294(2-Bromophenyl)boronic acid

생성물 1

HCID 580672832-Bromo-4'-tert-butylbiphenyl수율 55.1%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
85 °C

실험 절차

To a 250-mL, round bottom flask equipped with a magnetic stir bar was added water (41 mL) and 1,2-dimethoxyethane (41 mL). The solution was sparged with nitrogen for 20 minutes, then potassium carbonate (6.49 g, 46.9 mmol, 3 equiv), 2-bromophenylboronic acid (3.69 g, 18.4 mmol, 0.98 equiv) and 1-bromo-4-tert-butylbenzene (4.00 g, 18.8 mmol, 1 equiv) were added. The flask was then purged with N2 for 10 minutes before finally adding palladium(II) acetate (84 mg, 0.375 mmol, 0.02 equiv) and triphenylphosphine (394 mg, 1.50 mmol, 0.08 equiv). The reaction mixture was heated to 85 ° C. under a positive pressure of nitrogen for 18 hours. After cooling to room temperature, the phases were partitioned and the organic layer was collected. The aqueous layer was washed with ethyl acetate (3 ×20 mL). The combined organic fractions were washed with brine (50 mL), dried over sodium sulfate, filtered, and concentrated on a rotary evaporator. The crude yellow oil was purified by column chromatography on an Isco CombiFlash system (120-g column; eluted with 14 column volumes heptane) to afford the title compound as a colorless oil (2.93 g, 67 area % by HPLC, 54% yield). 1NMR (400 MHz, CDCl3) δ ppm 7.68 -7.64 (m, 1H), 7.48 -7.42 (m, 2H), 7.39 -7.31 (m, 4H), 7.21 -7.15 (m, 1H), 1.39 (s, 9H).

후처리

  1. customTo a 250-mL, round bottom flask equipped with a magnetic stir bar
  2. customThe solution was sparged with nitrogen for 20 minutes
  3. temperatureAfter cooling to room temperature
  4. customthe phases were partitioned
  5. customthe organic layer was collected
  6. washThe aqueous layer was washed with ethyl acetate (3 ×20 mL)
  7. washThe combined organic fractions were washed with brine (50 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated on a rotary evaporator
  11. customThe crude yellow oil was purified by column chromatography on an Isco CombiFlash system (120-g column; eluted with 14 column volumes heptane)

출처 및 근거

ORD 기록
ord-02d7e6e2d51045978d602e0f252aedd5
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200021B2

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