Bromobenzene → [1,1'-Biphenyl]-3-carbonitrile

HRID 2080039

반응식

HRID 2080039 반응식
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)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.O>[C:5]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1

참가 물질

8

반응물 4

HCID 7961BromobenzeneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27343253-Cyanophenylboronic acid

생성물 1

HCID 34340[1,1'-Biphenyl]-3-carbonitrile수율 67.3%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-cyanophenylboronic acid (1.0 g, 6.81 mmol) and bromobenzene (1.07 g, 6.81 mmol) in N,N-dimethylformamide (100 mL) were added tetrakis(triphenylphosphine)palladium(0) (0.393 g, 0.341 mmol) and cesium carbonate (2.77 g, 8.51 mmol) under nitrogen atmosphere, and the mixture was stirred for 4 hours under reflux. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), and biphenyl-3-carbonitrile (821 mg, 67%) was obtained as a yellow solid.

후처리

  1. temperatureunder reflux
  2. customwas allowed to room temperature
  3. customfor partitioning
  4. washthe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-2cd821fa646f4c25874bd3000f655fec
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

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