4-Nitrobenzoyl chloride → Methanone, (4-fluorophenyl)(4-nitrophenyl)-

HRID 729943Notes

Reaction equation

HRID 729943 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl-].[Al+3].[Cl-].[Cl-].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>[N+](CC)([O-])=O>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:8]([C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:9])=[CH:20][CH:19]=1

Participants

5

Reactant 3

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

Product 1

HCID 97658Methanone, (4-fluorophenyl)(4-nitrophenyl)-Yield 65%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

To a solution of 4-nitrobenzoyl chloride (2.3 g, 13 mmol) in nitroethane (20 mL) was added aluminum chloride (3.5 g, 26 mmol) followed by fluorobenzene (1.2 mL, 13 mmol). The mixture was stirred at rt for 4 h, then quenched carefully with 6M HCl. The reaction mixture was washed with dilute aqueous NaOH and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide the crude product as a light yellow solid. The solid was purified by recrystallization from hexanes to give (4-fluoro-phenyl)-(4-nitrophenyl)-methanone (2.0 g, 65%). 1H NMR (CHCl3-d) δ 8.41-8.32 (m, 5H), 7.90 (m, 1H), 7.84 (m, 1H), 7.20 (m, 1H).

Workup

  1. customquenched carefully with 6M HCl
  2. washThe reaction mixture was washed with dilute aqueous NaOH and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide the crude product as a light yellow solid
  7. customThe solid was purified by recrystallization from hexanes

Sources & evidence

ORD record
ord-7f2e80222af0498297bfef33d57ce2fd
Source dataset
uspto-grants-2009_09
Patent number
US07582646B2

Reaction notes

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