Nitrobenzene → 1-(3-Fluoro-4-methoxy-phenyl)-5-methyl-hexan-1-one

HRID 1900139Notes

Reaction equation

HRID 1900139 reaction equation
[N+](C1C=CC=CC=1)([O-])=O.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:14][CH:15]([CH3:22])[CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20].[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31]>>[F:23][C:24]1[CH:29]=[C:28]([C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH:15]([CH3:22])[CH3:14])[CH:27]=[CH:26][C:25]=1[O:30][CH3:31]

Participants

5

Reactant 4

HCID 7416Nitrobenzene2×HCID 675762-FluoroanisoleHCID 6451240Aluminum(III) ChlorideHCID 136648655-Methylhexanoyl chloride

Product 1

HCID 190437661-(3-Fluoro-4-methoxy-phenyl)-5-methyl-hexan-1-one

Procedure

14 ml of nitrobenzene are cooled in an ice-bath and then mixed in succession with 3.8 g of AlCl3 and 3.7 g of 5-methyl-hexanoyl chloride in 5 mi of nitrobenzene. The mixture is stirred and then treated with 2.7 ml of 2-fluoro-anisole. The solution is stirred overnight, then poured into ice-water and extracted with methylene chloride. The extracts are washed with water and 10% aqueous NaCl solution, and thereafter dried and concentrated and recrystallized using pentane. 5.31 g of 1-(3-fluoro-4-methoxy-phenyl)-5-methyl-hexan-l-one, MS: m/e 238 (M+), are obtained.

Workup

  1. stirringThe solution is stirred overnight
  2. extractionextracted with methylene chloride
  3. washThe extracts are washed with water and 10% aqueous NaCl solution
  4. customdried
  5. concentrationconcentrated
  6. customrecrystallized

Sources & evidence

ORD record
ord-58b3f30a1acd4a52bdad9a21faed2aca
Source dataset
uspto-grants-1996_11
Patent number
US05574071

Reaction notes

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