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Potassium Carbonate → 3-Amino-[1,1'-biphenyl]-4-carbonitrile

HRID 49419
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HRID 49419 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:3]=1[C:4]#[N:5].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.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>[NH2:1][C:2]1[CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 4297402-Amino-5-bromobenzonitrile

생성물 1

HCID 4594203-Amino-[1,1'-biphenyl]-4-carbonitrile수율 91.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 962
Water
용매
HCID 18180031Water 1,2-dimethoxyethane용매

실험 절차

A mixture of 2-amino-5-bromobenzonitrile (1.0 g, 5 mmol), phenylboronic acid (0.92 g, 7.5 mmol), tetrakis(triphenylphosphine)palladium (50 mg) and potassium carbonate (3.5 g, 25 mmol) in dimethoxyethane/water 2:1 (60 mL) was heated at reflux for 4 hours. After cooling to room temperature the reaction was diluted with water and extracted with ethyl acetate. The organic phase was dried and solvent evaporated. Trituation with petroleum ether gave 0.89 g of the desired compound.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was dried
  5. customsolvent evaporated

출처 및 근거

ORD 기록
ord-43571aa1299844ef8868ff4d26bf2b83
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06706749B2

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