Hydrochloric Acid → Methanone, (4-fluorophenyl)(4-nitrophenyl)-

HRID 993373Notes

Reaction equation

HRID 993373 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C(=S)=S.O>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:12]([C:11]2[CH:15]=[CH:16][C:8]([N+:5]([O-:7])=[O:6])=[CH:9][CH:10]=2)=[O:13])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 10008FluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 97658Methanone, (4-fluorophenyl)(4-nitrophenyl)-Yield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Procedure

Aluminum chloride (26.0 g, 195 mmol) was added in portions to a solution of 4-nitrobenzoyl chloride (27.8 g, 150 mL) and 4-fluorobenzene (15.8 g, 165 mmol) in carbon disulfide (100 mL). After 1 hour, the resulting yellow mixture was carefully treated with concentrated hydrochloric acid (60 mL) and stirred for 30 minutes. The mixture was then diluted with water and extracted with ethyl acetate. The organic layer was washed with dilute sodium hydroxide solution, water and brine, dried (MgSO4), and the solvent removed in vacuo. Crystallization from ethyl ether/hexanes gave 4-(4-fluorobenzoyl)-nitrobenzene (10.6 g, 82%) as a white solid, m.p. 87-88° C.; Analysis for C13H8NO3F: Calc.: C, 63.69; H, 3.26; N, 5.74: Found: C, 63.89; H, 3.28; N, 5.78.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with dilute sodium hydroxide solution, water and brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customCrystallization from ethyl ether/hexanes

Sources & evidence

ORD record
ord-69e4b85ce3584a4581367e40e25d38ce
Source dataset
uspto-grants-2002_10
Patent number
US06472536B1

Reaction notes

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