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

HRID 269522

반응식

HRID 269522 반응식
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]

참가 물질

8

반응물 3

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

생성물 1

HCID 587309812'-Bromobiphenyl-3-carboxylic acid ethyl ester수율 67.8%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 882672-Methylphenethyl alcohol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f00d8cdedfc244c2b1157fa02a493e53
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446222B2

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