2-Bromo-1-(4-fluorophenyl)ethan-1-one → 4-(4-Fluorophenyl)-1,3-oxazole

HRID 895369Notes

Reaction equation

HRID 895369 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[CH:12]([O-:14])=O.[NH4+:15]>C(O)=O>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:15]=[CH:12][O:14][CH:2]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 2723923Ammonium formate

Product 1

HCID 219311524-(4-Fluorophenyl)-1,3-oxazoleYield 22%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2-Bromo-1-(4-fluoro-phenyl)-ethanone (10 grams, 46 mmol), ammonium formate (11 grams, 175 mmol) and formic acid (60 mL) were added to a flask. The mixture was heated to reflux for 3.5 hours. The reaction was then cooled and quenched with 200 mL water. The pH was adjusted to 8 with 50% aqueous sodium hydroxide, and the aqueous layer was extracted with methylene chloride (3×200 mL). The combined organic extracts were dried over sodium sulfate, and concentrated under vacuum. The crude, red solid obtained was choursomatographed on silica gel (ISCO MPLC purification, 50 minutes., 0-25% ethyl acetate gradient, Biotage flash 40 m column) to provide 1.62 grams (22%) of the title compound. MS m/z: ESI+ 164.1 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. temperatureThe reaction was then cooled
  4. customquenched with 200 mL water
  5. extractionthe aqueous layer was extracted with methylene chloride (3×200 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe crude, red solid obtained
  9. customwas choursomatographed on silica gel (ISCO MPLC purification, 50 minutes., 0-25% ethyl acetate gradient, Biotage flash 40 m column)

Sources & evidence

ORD record
ord-01f9752d97a74d43946cc600eb630c62
Source dataset
uspto-grants-2005_07
Patent number
US06916807B2

Reaction notes

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