(4-Bromophenyl)(4-chlorophenyl)methanone → 4-Chloro-4'-isopropylbenzophenone

HRID 446217Notes

Reaction equation

HRID 446217 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH:17]([Mg]Cl)([CH3:19])[CH3:18]>O1CCCC1.[Ni](Cl)Cl.C1(P(C(P(C2C=CC=CC=2)C2C=CC=CC=2)(C)C)C2C=CC=CC=2)C=CC=CC=1>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:17]([CH3:19])[CH3:18])=[CH:3][CH:4]=2)=[O:9])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 2756868(4-Bromophenyl)(4-chlorophenyl)methanoneHCID 178418918HCID 178418918, compound

Product 1

HCID 27576234-Chloro-4'-isopropylbenzophenoneYield 198%

Reagents, catalysts & solvents 2

HCID 131730689HCID 131730689, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(4-bromophenyl)(4-chlorophenyl)methanone (10.0 g, 12.3 mmol) and bis(diphenylphosphino)propane nickel(II) chloride (0.4 g, 0.7 mmol) were dissolved in purified tetrahydrofuran (200 mL) under a nitrogen atmosphere, and isopropyl magnesium chloride (18.7 mL, 37.4 mmol) was slowly added thereto at 0° C. The reaction mixture solution was stirred at room temperature for 24 hours. The reaction mixture solution was subjected to extraction with dichloromethane and distilled water, and the extracted material was subjected to column chromatography (hexane:ethylacetate=8:2). The reaction solvent was removed, and then the residue material was dried in vacuum to thereby obtain a white solid (6.3 g, yield: 72%).

Workup

  1. customat 0° C
  2. extractionThe reaction mixture solution was subjected to extraction with dichloromethane
  3. distillationdistilled water
  4. customThe reaction solvent was removed
  5. customthe residue material was dried in vacuum

Sources & evidence

ORD record
ord-a921723b4f7c4fc99175605abb39d337
Source dataset
uspto-grants-2013_07
Patent number
US08476474B2

Reaction notes

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