Water → 4-Fluoro-4'-methylbenzophenone

HRID 502491Notes

Reaction equation

HRID 502491 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[F:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.O>C(Cl)Cl.CCCCCC>[CH3:11][C:5]1[CH:10]=[CH:9][C:8]([C:17]([C:16]2[CH:20]=[CH:21][C:13]([F:12])=[CH:14][CH:15]=2)=[O:18])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 47290124-Fluoro-4'-methylbenzophenoneYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

Aluminum chloride (3.74 g, 28 mmol) was added into a stirred solution of toluene 18 (60 mL) and 4-fluorobenzoyl chloride (3.42 g, 21.6 mmol). The solution was stirred at room temperature for 90 minutes, and then 5 mL of water was added dropwise to quench the reaction. The reaction mixture washed with water and 10% NaHCO3. The solution was then dried with anhydrous MgSO4. The solvent was removed from the solution to obtain a yellow solid. The yellow crude product was dissolved in a small amount of methylene chloride and hexane was added dropwise until precipitation occurred. The solution was then heated and the product was allowed to recrystallize to form 2.70 g of product (62% yield). 1H-NMR: δ 7.80 (dd, aromatic, 2H), 7.67 (d, aromatic, 2H), 7.26 (d, aromatic, 2H), 7.15 (t, aromatic, 2H), 2.42 (s, methyl, 3H). 13C-NMR: δ 195.0 (carbonyl); 166.2, 164.2, 143.3, 134.7, 132.2, 130.1, 129.0, 115.3 (aromatic); 21.6 (alkyl). 19F-NMR: δ −109.1 ppm.

Workup

  1. customto quench
  2. customthe reaction
  3. washThe reaction mixture washed with water and 10% NaHCO3
  4. dry with materialThe solution was then dried with anhydrous MgSO4
  5. customThe solvent was removed from the solution
  6. customto obtain a yellow solid
  7. additionwas added dropwise until precipitation
  8. temperatureThe solution was then heated
  9. customto recrystallize

Sources & evidence

ORD record
ord-65260a35bd5040d59eb02ff926c6465a
Source dataset
uspto-grants-2010_08
Patent number
US07776535B2

Reaction notes

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