Sodium Carbonate → HCID 67254694、化合物

HRID 536617ノート

反応式

HRID 536617 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 67254694HCID 67254694、化合物収率 69%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 86587398Ethanol toluene water溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3eacde70836241928a06b88412f43348
出典データセット
uspto-grants-2014_10
特許番号
US08859611B2

反応ノート

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