Hydrochloric Acid → (4-Bromophenyl)(4-fluorophenyl)methanone

HRID 35989

Reaction equation

HRID 35989 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10008FluorobenzeneHCID 685154-Bromobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 74951(4-Bromophenyl)(4-fluorophenyl)methanoneYield 86%

Conditions

Temperature
0 °C

Procedure

In a 250 mL flask equipped with a nitrogen inlet, overhead stirring assembly, and reflux condenser were placed fluorobenzene (117 g, 1.2 mol) and 4-bromobenzoyl chloride (39.8 g, 0.181 mol). The mixture was cooled to 0° C. and aluminum chloride (27 g, 0.20 mol) was added. The mixture was stirred for 15 minutes at 23° C., followed by heating to reflux for 4 h. The reaction was then cooled to 23° C. and stirred for 16 h. 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 to yield an off white powder. Recrystallization from ethanol afforded 43.3 g (86%) of 4-bromo-4'-fluorobenzophenone as white crystals: m.p. 106°-107° C., (Lit. 107°-108° C.).

Workup

  1. customIn a 250 mL flask equipped with a nitrogen inlet
  2. temperaturereflux condenser
  3. stirringThe mixture was stirred for 15 minutes at 23° C.
  4. temperatureby heating
  5. temperatureto reflux for 4 h
  6. temperatureThe reaction was then cooled to 23° C.
  7. stirringstirred for 16 h
  8. extractionThe organics were extracted with methylene chloride
  9. dry with materialdried over magnesium sulfate
  10. filtrationThe slurry was filtered
  11. customthe methylene chloride was removed under reduced pressure
  12. customto yield an off white powder
  13. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-52ddc66d1eb0405192a178ae86bfd4f9
Source dataset
uspto-grants-1995_05
Patent number
US05412066

Linked notes

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