4-Bromobiphenyl → 1-(1,1'-Biphenyl)-4-yl-2-phenylethan-1-one

HRID 924938Notes

Reaction equation

HRID 924938 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Li]CCCC.C1([C:25](=[O:34])[CH2:26][C:27]2[CH:28]=[C:29](C)[CH:30]=[CH:31][CH:32]=2)C=CC=CC=1>C1COCC1>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]([C:25](=[O:34])[CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 71014-BromobiphenylHCID 131736142-(3-Methylphenyl)acetophenone2×HCID 178418339Butyllithium

Product 1

HCID 748171-(1,1'-Biphenyl)-4-yl-2-phenylethan-1-oneYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromobiphenyl (683 mg, 2.9 mmol) in anhydrous THF (5 mL) was added n-BuLi (1.2 mL, 2.9 mmol) dropwise at −78° C. After being stirred at the temperature for 0.5 h, a solution of N-methoxy-N-methyl-2-phenyl-acetamide (prepared following step 1 of Intermediate 4) (500 mg, 2.8 mmol) in anhydrous THF (5 mL) was added via a syringe, and the mixture was stirred at −78° C. for 2 h. The reaction was quenched with saturated NH4Cl aqueous solution, and extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE:EtOAc=20:1) to give 1-(biphenyl-4-yl)-2-phenylethanone (180 mg, yield 24%).

Workup

  1. stirringthe mixture was stirred at −78° C. for 2 h
  2. customThe reaction was quenched with saturated NH4Cl aqueous solution
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (PE:EtOAc=20:1)

Sources & evidence

ORD record
ord-cdd19428d3154f77974e384f5be451fd
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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