6-Fluoro-2-(1-hydroxyethyl)benzoxazole → 2-Acetyl-6-fluorobenzoxazole

HRID 369105Notes

Reaction equation

HRID 369105 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]2[N:6]=[C:7]([CH:9]([OH:11])[CH3:10])[O:8][C:4]=2[CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[C:9]([C:7]1[O:8][C:4]2[CH:3]=[C:2]([F:1])[CH:13]=[CH:12][C:5]=2[N:6]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 232854276-Fluoro-2-(1-hydroxyethyl)benzoxazoleHCID 178418287HCID 178418287, compound

Product 1

HCID 232853722-Acetyl-6-fluorobenzoxazoleYield 41.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

6-Fluoro-2-(1-hydroxyethyl)benzoxazole (4.71 g, 26 mmol) was dissolved in 100 ml of methylene chloride, and pyridinium chlorochromate (8.38 g, 39 mmol) was added portionwise to the solution. The mixture was stirred for 4 hours at room temperature, then diluted with ether, and filtered. The filtrate was concentrated and the resulting residue was subjected to column chromatography and then recrystallization from methanol to afford 2-acetyl-6-fluorobenzoxazole (1.92 g, yield: 41%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customrecrystallization from methanol

Sources & evidence

ORD record
ord-ee9da078519246658f996d007ecf3d0f
Source dataset
uspto-grants-2000_10
Patent number
US06136831

Reaction notes

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