1,2-二溴苯 → 2'-Bromobiphenyl-3-carboxylic acid ethyl ester

HRID 269522

反应方程式

HRID 269522 反应方程式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Br:8].[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)=[O:13])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.C(OCC)(=O)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>[CH2:9]([O:11][C:12]([C:14]1[CH:19]=[C:18]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[Br:8])[CH:17]=[CH:16][CH:15]=1)=[O:13])[CH3:10]

参与物

8

反应物 3

HCID 114141,2-二溴苯HCID 11430碳酸钾HCID 32493123-乙氧羰基苯硼酸

产物 1

HCID 587309812'-Bromobiphenyl-3-carboxylic acid ethyl ester收率 67.8%

试剂、催化剂与溶剂 4

HCID 178418397HCID 178418397，化合物催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8857乙酸乙酯溶剂HCID 88267邻甲基苯乙醇溶剂

实验过程

A mixture of 1,2-dibromobenzene (0.63 ml, 5.2 mmol), (3-ethoxycarbonylphenyl)boronic acid (506 mg, 2.6 mmol), tetrakis(triphenylphosphine)palladium(0) (640 mg, 0.6 mmol) and potassium carbonate (2.879 g, 20.9 mmol) was heated in toluene-ethanol (1:1, 10 ml at 90° C. for 3 hours. Upon cooling, the mixture was diluted with ethyl acetate and water. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography using Biotage with iso-hexane containing a gradient of DCM (2-15%) to yield the title compound (538 mg, 34%).

后处理

  1. temperatureUpon cooling
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography

来源与证据

ORD记录
ord-f00d8cdedfc244c2b1157fa02a493e53
来源数据集
uspto-grants-2008_11
专利号
US07446222B2

关联笔记

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