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1,2-Dibromobenzene → 2'-Bromo-biphenyl-3-carbonitrile

HRID 269539
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인쇄 미리보기

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HRID 269539 반응식
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1Br.C1(C)C=CC=CC=1.C(O)C>C(OCC)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>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1
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참가 물질

7

반응물 3

HCID 114141,2-DibromobenzeneHCID 27343253-Cyanophenylboronic acidHCID 21863594Toluene ethanol

생성물 1

HCID 13924952'-Bromo-biphenyl-3-carbonitrile수율 69.3%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962
Water
용매
HCID 3283Diethyl Ether용매

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온도
90 °C

실험 절차

A mixture of 3-cyanophenylboronic acid (735 mg, 5 mmol), 1,2-dibromobenzene (2.36 g, 10 mmol) potassium carbonate (6.9 g, 50 mmol) and tetrakis(triphenylphosphine)palladium(0) (580 mg, 0.5 mmol) in 1:1 toluene/ethanol (40 ml) was stirred and heated at 90° C. under nitrogen for 3 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was purified by chromatography using Biotage with ethyl acetate/iso-hexane (1:19) to yield the title compound as a white solid (895 mg 69%).

후처리

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (MgSO4)
  3. customevaporated to dryness
  4. customThe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-61ef2a173c7c443d8121534960b66168
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07446222B2

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