HRID1628369

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID8028

Tetrahydrofuran

C4H8O

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CC(C)(C)c1ccc(-c2nc(-c3ccc(Br)cc3)nc(-c3ccc(C(C)(C)C)cc3)n2)cc1

HCID59439787

未命名化合物

HCID66674744

未命名化合物

PRODUCTS

生成物

结构：C=Cc1ccc(-c2ccc(-c3nc(-c4ccc(C(C)(C)C)cc4)nc(-c4ccc(C(C)(C)C)cc4)n3)cc2)cc1

HCID59439782

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

PROCEDURE

实验过程

2.0 g (0.0040 mol) of 2-(4-bromophenyl)-4,6-bis-(4-tert-butylphenyl)-1,3,5-triazine and 0.8878 g (0.006 mol) of vinylphenylboronic acid and 0.050 g (0.0432 mmol) of Pd(PPh3)4 are initially introduced. After addition of 26 ml of sodium carbonate solution and 54 ml of THF, the mixture is brought to reaction under reflux for 24 h. For work-up, the mixture is filtered through Celite and taken up in ethyl acetate. The organic phase is extracted a number of times with water. The solvent of the combined organic phases is removed completely. A recrystallisation is carried out from chloroform/ethanol, and subsequent column chromatography is carried out with hexane:ethyl acetate. After the column chromatography, 1.6 g (76%) of clean substance are isolated.

WORKUP

后处理

customthe mixture is brought to reaction
temperatureunder reflux for 24 h
filtrationFor work-up, the mixture is filtered through Celite
extractionThe organic phase is extracted a number of times with water
customThe solvent of the combined organic phases is removed completely
customA recrystallisation
customAfter the column chromatography, 1.6 g (76%) of clean substance are isolated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-639465824ba44125be47b249a50c6c3c
来源数据集: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08786181B2
来源说明: uspto-grants-2014_07

反应 SMILES

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=3)[N:11]=[C:10]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=3)[N:9]=2)=[CH:4][CH:3]=1.C(OB([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)O)=C.C(=O)([O-])[O-].[Na+].[Na+].[CH2:51]1COC[CH2:52]1>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:20]([C:17]1[CH:18]=[CH:19][C:14]([C:12]2[N:11]=[C:10]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:28][CH:29]=3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:42]4[CH:41]=[CH:40][C:39]([CH:51]=[CH2:52])=[CH:44][CH:43]=4)=[CH:3][CH:4]=3)[N:13]=2)=[CH:15][CH:16]=1)([CH3:22])([CH3:23])[CH3:21]