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

HRID 1358808Notes

Reaction equation

HRID 1358808 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, 5.71: 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-02e4441388694afa9f1dca397fa953d1
Source dataset
uspto-grants-2003_07
Patent number
US06596876B2

Reaction notes

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