Fluorobenzene → 2,5-dichloro-4'-fluorobenzophenon

HRID 1026374Notes

Reaction equation

HRID 1026374 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:8][C:9]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=1[C:11](Cl)=[O:12].[Cl-].[Al+3].[Cl-].[Cl-]>O>[Cl:8][C:9]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=1[C:11]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:12]

Participants

5

Reactant 3

HCID 10008FluorobenzeneHCID 179452,5-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 120399992,5-dichloro-4'-fluorobenzophenon

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

Into a 2 L three-neck flask equipped with a stirrer, a thermometer and a nitrogen-introducing tube, 240.2 g (2.50 mol) of fluorobenzene was introduced, and was cooled to 10° C. in an ice bath. Then, 134.6 g (0.50 mol) of 2,5-dichlorobenzoic acid chloride, and 86.7 g (0.65 mol) of aluminum chloride were slowly added such that the reaction temperature would not exceed 40° C. After the addition, the mixture was stirred at 40° C. for 8 hours. After the disappearance of the raw materials was confirmed by thin-layer chromatography, the mixture was dropped in iced water, and extraction using ethyl acetate was carried out. The extraction liquid was neutralized by 5% sodium bicarbonate water, and the resultant was washed with saturated saline water. The liquid washed was dried with magnesium sulfate, and then the solvent was distilled away using an evaporator. The residue was allowed to recrystallize in methanol, thereby an intermediate product, 2,5-dichloro-4′-fluorobenzophenone, was obtained. Amount obtained was 130 g, and yield percentage was 97%. Note that, the yield percentage was calculated by following formula (hereinafter, the same): yield percentage (%)=(amount of product obtained/theoretical amount of product)×100.

Workup

  1. customInto a 2 L three-neck flask equipped with a stirrer
  2. additiona thermometer and a nitrogen-introducing tube
  3. customexceed 40° C
  4. additionAfter the addition
  5. extractionextraction
  6. extractionThe extraction liquid
  7. washthe resultant was washed with saturated saline water
  8. washThe liquid washed
  9. dry with materialwas dried with magnesium sulfate
  10. distillationthe solvent was distilled away
  11. customan evaporator
  12. customto recrystallize in methanol

Sources & evidence

ORD record
ord-09048a8522e543d8a502c6409412dced
Source dataset
uspto-grants-2014_05
Patent number
US08729219B2

Reaction notes

Loading…