Reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11](C#CC3C=CC=CC=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.FC1C=CC=CC=1.[Br:31]C1C=CC(CCl)=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[Br:31][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:22]=[CH:23][C:2]([F:1])=[CH:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1Participants
Procedure
Synthesis of 4-fluoro-4'-phenylethynylbenzophenone In a 250 mL flask equipped with a nitrogen inlet, overhead stirring assembly, and reflux condenser was placed fluorobenzene (117 g, 1.2 mol), and 4-bromobenzyl chloride (39.8 g, 0.181 mol). The mixture was cooled to 0° C. an anhydrous aluminum chloride (27 g, 0.20 mol) was added. The mixture was stirred at 23° C. for 16 hours. The resulting slurry was poured into 2 L of acidic (HCl) water. The organics were extracted with methylene chloride, and dried over magnesium sulfate. The slurry was filtered and the methylene chloride was removed under reduced pressure. Recrystallization from ethanol afforded 43.3 g (86%) of 4-bromo-4'-fluorobenzophenone as white crystals: mp 106°-107° C. (Lit 107°-108° C.).
Workup
- customequipped with a nitrogen inlet
- temperaturereflux condenser
- additionwas added
- stirringThe mixture was stirred at 23° C. for 16 hours
- extractionThe organics were extracted with methylene chloride
- dry with materialdried over magnesium sulfate
- filtrationThe slurry was filtered
- customthe methylene chloride was removed under reduced pressure
- customRecrystallization from ethanol
Sources & evidence
- ORD record
- ord-d03901bcb5e142568d70254e005582fc
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05312994
Linked notes
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