HRID983808

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6422

未命名化合物

HCID66827

Boronic acid, phenyl-

C6H7BO2

HCID18373917

Acetonitrile--water (1/1)

C2H5NO

HCID54469909

未命名化合物

PRODUCTS

生成物

结构：COCCOCOc1c(C=O)cc(CC(=O)OC)cc1-c1ccccc1

HCID54196773

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

溶剂HCID1140

Toluene

C7H8

溶剂HCID11430

Potassium Carbonate

CK2O3

CONDITIONS

反应条件

温度: 70 °C

PROCEDURE

实验过程

The arylbromide (5) (118 mmol, 42.6 gr) was dissolved in about 430 ml of toluene in a 1 L flask to which 150 ml of 2M K2CO3 was added followed by 5.0 g (0.037 eq) of Pd(PPh3)4. After the addition of phenylboronic acid (2.0 eq, 29 gr) the flask was heated to 70° C. and the mixture stirred for 5 hours. HPLC of the reaction mixture indicated that the arylbromide had completely reacted and a dominant less polar moiety (89% pure, r.t.=8.5 min., 1-90% MeCN/H2O, 0.1% TFA) was observed.

WORKUP

后处理

additionwas added
customhad completely reacted

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-38d3785efda347b398acf25214fa01ae
来源数据集: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06867200B1
来源说明: uspto-grants-2005_03

反应 SMILES

[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[C:9]([CH:11]=[O:12])[C:8]([O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:7](Br)[CH:6]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC#N.O.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].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>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:6]=[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:8]([O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:9]([CH:11]=[O:12])[CH:10]=1