Hydrochloric Acid → 3-Fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)nitrobenzene

HRID 1584342Notes

Reaction equation

HRID 1584342 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][C:9]=1F.[CH3:14][C:15]1[O:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:17][C:16]=1[CH2:26][OH:27].Cl>CN(C)C=O>[F:3][C:4]1[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:8][C:9]=1[O:27][CH2:26][C:16]1[N:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:19][C:15]=1[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 115719324-(Hydroxymethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 110348083-Fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)nitrobenzeneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 2.2 g) was added portionwise, at 0° C., to a solution of 3,4-difluoronitrobenzene (8.8 g) and 5-methyl-2-phenyl-4-oxazolyl methanol (10.0 g) in N,N-dimethylformamide (DMF) (100 ml). The mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into ice-water, which was acidified with 2N HCl. Then, resulting crystalline precipitate was collected by filtration, which was recrystallized from dichloromethane-methanol to give 3-fluoro-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)nitrobenzene (14.0 g, 81%) as colorless prisms, m.p.155-156° C.

Workup

  1. customThen, resulting crystalline precipitate
  2. filtrationwas collected by filtration, which
  3. customwas recrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-97570538177d482bb3355da1c07d1863
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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