Sodium Carbonate → 4'-Methoxy-3-methyl-1,1'-biphenyl-4-carbonitrile

HRID 1064745

반응식

HRID 1064745 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>C1C=CC=CC=1.C(O)C.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>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=2)=[CH:21][CH:20]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 1442674-Bromo-2-methylbenzonitrileHCID 201262(4-Methoxyphenyl)boronic acid

생성물 1

HCID 112183464'-Methoxy-3-methyl-1,1'-biphenyl-4-carbonitrile수율 102.7%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매HCID 702Ethanol용매

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온도
75 °C

실험 절차

4-Bromo-2-methylbenzonitrile (4.9 g, 25.0 mmol), Pd(PPh3)4 (578 mg) in benzene (50 mL) and 2.0 M aqueous solution of Na2CO3 (25 mL, 50.0 mmol) was treated with 4-methoxyphenylboronic acid (4.56 g, 30.0 mmol) in ethanol (20 mL) and heated at 75° C. for 17 hours. The mixture was allowed to cool to room temperature and the phases were separated. The aqueous phase was extracted with diethyl ether (3×40 mL). The original benzene layer and the diethyl ether extracts were combined, filtered over celite, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography over silica using a mixture of hexane/CH2Cl2 (3:1) to provide the title compound as a white powder (5.73 g, 85% yield). 1HNMR (300 MHz, CDCl3) δ 2.35 (3H), 3.70 (s, 3H), 6.80-7.50 (m, 7H); MS (DCI) m/z 224 (M+H)+.

후처리

  1. temperatureto cool to room temperature
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with diethyl ether (3×40 mL)
  4. filtrationfiltered over celite
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by chromatography over silica using
  9. additiona mixture of hexane/CH2Cl2 (3:1)

출처 및 근거

ORD 기록
ord-e29f2c73feb0419498af6bf12b410522
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969730B2

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