Water → 6-Fluoro-3-(3-methoxy-phenyl)-benzo[d]isoxazole

HRID 852079Notes

Reaction equation

HRID 852079 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=[N:10][OH:11].CC(C)([O-])C.[K+].C(OCC)(=O)C.O>O1CCCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[N:10][O:11][C:2]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 72465824(2,4-Difluoro-phenyl)-(3-methoxy-phenyl)-methanone oxime

Product 1

HCID 179062626-Fluoro-3-(3-methoxy-phenyl)-benzo[d]isoxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Cool (2,4-difluoro-phenyl)-(3-methoxy-phenyl)-methanone oxime (52.66 g, 217 mmol) in tetrahydrofuran (500 mL) to 0° C. Add 1.0 M solution of potassium tert-butoxide in tetrahydrofuran (260 mL, 0.26 mol) and stir at room temperature for 1.5 hours. Reflux reaction mixture for an additional 1.5 hours. Cool to room temperature overnight. Dilute reaction mixture with ethyl acetate and water and separate. Dry the organic layer and concentrate to give the title compound as an oil. Purify by column chromatography (dichloromethane) and triturate with pentane to give the title compound as a white solid (30.2 g, 62% Yield). NMR and M/S are consistent with the final, desired compound. mp=68-69° C.

Workup

  1. temperatureReflux
  2. customreaction mixture for an additional 1.5 hours
  3. temperatureCool to room temperature overnight
  4. additionDilute
  5. customseparate
  6. customDry the organic layer
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-d23042a69e9341eaacf5cf25b1c49686
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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