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

HRID 1384731Notes

Reaction equation

HRID 1384731 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.[Al+3].[Cl-].[Cl-].[Cl-].Cl>O>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10008Fluorobenzene2×HCID 685154-Bromobenzoyl chloride2×HCID 6451240Aluminum(III) Chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4-bromo-4′-fluorobenzophenone was synthesized by the Friedel-Crafts acylation of fluorobenzene with 4-bromobenzoyl chloride. More specifically, fluorobenzene (117 grams, 1.2 mol) and 4-bromobenzoyl chloride (39.8 grams, 0.18 mol) was charged to a 250 milliliter flask equipped with a mechanical stirrer, N2 inlet, and reflux condenser. The mixture was then cooled to 0° C. and anhydrous AlCl3 (27 grams, 0.20 mol) was added. The mixture was stirred for 15 minutes at 23° C. for 16 hours. The resulting slurry was poured into 2 liters of water acidified with HCl. The organics were extracted with methylene chloride and subsequently dried over MgSO4. The slurry was filtered and the methylene chloride was removed under reduced pressure. Recrystallization from ethanol gave 43.4 grams (86 percent yield) of the desired crystalline product.

Workup

  1. customequipped with a mechanical stirrer, N2 inlet
  2. temperaturereflux condenser
  3. extractionThe organics were extracted with methylene chloride
  4. dry with materialsubsequently dried over MgSO4
  5. filtrationThe slurry was filtered
  6. customthe methylene chloride was removed under reduced pressure
  7. customRecrystallization from ethanol
  8. customgave 43.4 grams (86 percent yield) of the desired crystalline product

Sources & evidence

ORD record
ord-0b3b802f52164fde960c13bd3569c954
Source dataset
uspto-grants-2001_07
Patent number
US06260949B1

Reaction notes

Loading…