4-Nitrobenzoyl chloride → (3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-yl)-(4-nitro-phenyl)-methanone

HRID 1632066Notes

Reaction equation

HRID 1632066 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-].[Cl-].[Cl-].[Al+3].[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=2[O:31][CH3:32])[CH:21]=[CH:22][CH:23]=1>[N+](C1C=CC=CC=1)([O-])=O>[Cl:17][C:18]1[CH:19]=[C:20]([C:24]2[C:25]([O:31][CH3:32])=[CH:26][CH:27]=[C:28]([C:8]([C:7]3[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[O:9])[C:29]=2[F:30])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 580203133'-Chloro-6-fluoro-2-methoxy-biphenyl

Product 1

HCID 58019914(3'-Chloro-2-fluoro-6-methoxy-biphenyl-3-yl)-(4-nitro-phenyl)-methanoneYield 91%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

To a solution of 4-nitro-benzoyl chloride (1900 mg, 10.2 mmol) in nitrobenzene (6 mL) was added aluminum trichloride (1360 mg, 10.2 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred at room temperature for 1 h, cooled to 0° C., and 3′-chloro-6-fluoro-2-methoxy-biphenyl (2.01 g, 8.5 mmol) in nitrobenzene (1 mL) was added at 0° C. The reaction mixture was allowed to warm to room temperature and stirred 24 h. The reaction mixture was cooled to −10° C. and quenched with ice-water (50 mL), extracted with ethyl acetate (2×25 mL), washed with water (2×10 mL), saturated aqueuos sodium bicarbonate (10 mL), brine (30 mL), and dried over Na2SO4. After filtration and removal of solvent, the crude was purified by crystallization from ether-hexane to give I-133 (3.00 g, 91% yield).

Workup

  1. temperaturecooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred 24 h
  4. temperatureThe reaction mixture was cooled to −10° C.
  5. customquenched with ice-water (50 mL)
  6. extractionextracted with ethyl acetate (2×25 mL)
  7. washwashed with water (2×10 mL), saturated aqueuos sodium bicarbonate (10 mL), brine (30 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationAfter filtration and removal of solvent
  10. customthe crude was purified by crystallization from ether-hexane
  11. customto give I-133 (3.00 g, 91% yield)

Sources & evidence

ORD record
ord-fa1ba33d9765411ba0d66157ae3a9f2d
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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