POTASSIUM DIPHOSPHATE → 2',6'-Dimethyl-4'-[3-(methylthio)propoxy]-6-phenoxybiphenyl-3-carbaldehyde

HRID 15661

反应方程式

HRID 15661 反应方程式
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:5]=[O:6].[CH3:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][S:28][CH3:29])[CH:21]=[C:20]([CH3:30])[C:19]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][S:28][CH3:29])[CH:21]=[C:20]([CH3:30])[C:19]=1[C:2]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1

参与物

9

反应物 4

HCID 62657POTASSIUM DIPHOSPHATEHCID 112698722-双环己基膦-2',6'-二甲氧基联苯HCID 59342549{2,6-Dimethyl-4-[3-(methylthio)propoxy]phenyl}boronic acidHCID 593425893-Bromo-4-phenoxybenzaldehyde

产物 1

HCID 593426072',6'-Dimethyl-4'-[3-(methylthio)propoxy]-6-phenoxybiphenyl-3-carbaldehyde收率 70%

试剂、催化剂与溶剂 4

HCID 9811564三(二亚苄基丙酮)二钯催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂2 次HCID 1140甲苯溶剂HCID 8857乙酸乙酯溶剂

反应条件

温度
100 °C

实验过程

3-Bromo-4-phenoxybenzaldehyde (1.11 g, 4.00 mmol), {2,6-dimethyl-4-[3-(methylthio)propoxy]phenyl}boronic acid (1.02 g, 4.00 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.263 g, 0.640 mmol) and tripotassium phosphate (1.70 g, 8.00 mmol) were dissolved in a mixed solvent of toluene (20 mL) and water (4 mL). After argon substitution, tris(dibenzylideneacetone)dipalladium(0) (0.147 g, 0.160 mmol) was added. The reaction mixture was stirred at 100° C. for 18 hr under argon atmosphere. The reaction mixture was allowed to cool, and water was added. The mixture was diluted with ethyl acetate, and the insoluble substance was filtered off through celite. The organic layer of the filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80) to give the title compound (1.13 g, yield 70%) as a yellow oil.

后处理

  1. temperatureto cool
  2. filtrationthe insoluble substance was filtered off through celite
  3. washThe organic layer of the filtrate was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80)

来源与证据

ORD记录
ord-0307d4f4d8c845078368933bba8df6d5
来源数据集
uspto-grants-2010_06
专利号
US07732626B2

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