Benzyl Alcohol → HCID 23130305, compound

HRID 2114169Notes

Reaction equation

HRID 2114169 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:11][C:12]1[C:22](F)=[CH:21][C:15]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])=[C:14]([N+:24]([O-:26])=[O:25])[CH:13]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH2:3]([O:10][C:22]1[C:12]([F:11])=[CH:13][C:14]([N+:24]([O-:26])=[O:25])=[C:15]([CH:21]=1)[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 311Citric AcidHCID 24758Sodium hydrideHCID 231303114,5-difluoro-N,N-dimethyl-2-nitrobenzamide

Product 1

HCID 23130305HCID 23130305, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium hydride (209 mg) was suspended in DMF (10 mL), and to this suspension were added benzyl alcohol (564 mg) and a solution of 4,5-difluoro-N,N-dimethyl-2-nitrobenzamide (1.0 g) in DMF (3 mL). The mixture was stirred at 50° C. for 2 hours, and then cooled with ice. After addition of 10% aqueous citric acid, the reaction mixture was extracted with ethyl acetate and the extract was washed with water and aqueous brine, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:3) to give 5-benzyloxy-4-fluoro-N,N-dimethyl-2-nitrobenzamide (1.06 g).

Workup

  1. temperaturecooled with ice
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with water and aqueous brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:3)

Sources & evidence

ORD record
ord-d9e79f567a844d5592c9e0d45a468dea
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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