Sodium Carbonate → HCID 67254694, 화합물

HRID 2043373노트

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HRID 2043373 반응식
Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][CH:3]=1.[CH3:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1B1OC(C)(C)C(C)(C)O1)[C:12]#[N:13].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.CCOC(C)=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>[Br:7][C:6]1[C:2]([C:16]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH3:8])=[CH:3][S:4][CH:5]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 184523,4-DibromothiopheneHCID 567769293-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

생성물 1

HCID 67254694HCID 67254694, 화합물수율 69%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 86587398Ethanol toluene water용매

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온도
80 °C

실험 절차

A mixture of 3,4-dibromothiophene (3 g, 12.5 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (2 g, 12.5 mmol), Na2CO3 (2.7 g, 25 mmol), Pd(PPh3)4 (1.4 g, 1.25 mmol) in a mixture of toluene/EtOH/H2O (40 mL, 5:3:2) was stirred at 80° C. under nitrogen overnight. The reaction mixture was diluted with EtOAc (80 mL), and washed with water and brine. The organic phase was dried over Na2SO4, concentrated in vacuo, and purified on silica gel column (PE: EtOAc=30:1) to afford 4-(4-bromothiophen-3-yl)-3-methylbenzonitrile (Scheme III, 13, X1=4-cyano-2-methylphenyl) (2.4 g, yield 68%) as yellow oil. 1H NMR (CD3OD 400 MHz): δ 7.56 (s, 1H), 7.50-7.48 (m, 2H), 7.31 (d, J=3.2 Hz, 1H), 7.22 (d, J=7.6 Hz, 1H), 2.10 (s, 3H).

후처리

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified on silica gel column (PE: EtOAc=30:1)

출처 및 근거

ORD 기록
ord-569f34ac653044b0b66d6e024ff6c41a
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586624B2

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