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

HRID 269522

反応式

HRID 269522 の反応式
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]

参加物

8

反応物 3

HCID 114141,2-DibromobenzeneHCID 11430Potassium CarbonateHCID 3249312(3-Ethoxycarbonylphenyl)boronic acid

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 882672-Methylphenethyl alcohol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-f00d8cdedfc244c2b1157fa02a493e53
出典データセット
uspto-grants-2008_11
特許番号
US07446222B2

関連ノート

読み込み中…