Sodium Carbonate → 3-Isopropenylbenzonitrile

HRID 14082

반응식

HRID 14082 반응식
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]([CH3:15])=[CH2:14].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])([CH3:15])=[CH2:14]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 112022-BromopropeneHCID 27343253-Cyanophenylboronic acid

생성물 1

HCID 121802503-Isopropenylbenzonitrile

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a stirred solution of 3-cyanophenylboronic acid (10.0 g, 68.05 mmol) dissolved in DME (340 mL) is added 2-bromopropene (6.86 g, 56.7 mmol), and sodium carbonate (62.3 mL of a 2 M solution in water, 124.7 mmol). The reaction mixture is degassed for 20 min with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (2.54 g, 2.2 mmol) is added, the reaction mixture degassed for 10 min, and heated at reflux overnight. The reaction mixture is cooled to room temperature and then partitioned between hexanes and water. The aqueous layer is extracted with hexanes (3×75 mL). The combined organic layers are washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (9:1 hexanes/ethyl acetate) provides the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.96 (m, 1H), 7.85 (d, J=8 Hz, 1H), 7.75 (d, J=8 Hz, 1H), 7.56 (m, 1H) 5.58 (s, 1H), 5.23 (m, 1H), 2.13 (s, 3H).

후처리

  1. customThe reaction mixture is degassed for 20 min with nitrogen
  2. customthe reaction mixture degassed for 10 min
  3. temperatureheated
  4. temperatureat reflux overnight
  5. custompartitioned between hexanes and water
  6. extractionThe aqueous layer is extracted with hexanes (3×75 mL)
  7. washThe combined organic layers are washed with brine
  8. dry with materialdried (magnesium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customPurification by flash column chromatography (9:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-f63263e9904849a6be8ce23d03fbe3dc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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