Potassium tert-butoxide → HCID 90389418, compound

HRID 1526529Notes

Reaction equation

HRID 1526529 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([F:21])=[C:12]([C:14]2[CH2:18][CH:17]([CH2:19]Cl)[O:16][N:15]=2)[CH:13]=1>CS(C)=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([F:21])=[C:12]([C:14]2[CH:18]3[CH:17]([CH2:19]3)[O:16][N:15]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 64157865HCID 64157865, compound

Product 1

HCID 90389418HCID 90389418, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium t-butoxide (176 mg, 1.572 mmol, Aldrich) was added in small portions over a time period of 20 min to a solution of 3-(5-bromo-2-fluorophenyl)-5-(chloromethyl)-4,5-dihydroisoxazole (200 mg, 0.684 mmol, 1d rac) in DMSO (4 mL) cooled with a water bath. After completed, the reaction was quenched by the addition of ice. EtOAc was added and the organic phase was separated. The organic phase was dried over MgSO4 and the solvent was removed under reduced pressure. The crude material was absorbed onto a plug of silica gel and purified by chromatography, eluting with 3% to 5% EtOAc in hexane, to provide the title compound as a colorless oil (154 mg, 0.601 mmol, 88% yield). MS m/z=257.9 [M+H]+. Calculated for C10H7BrFNO: 256.07.

Workup

  1. temperaturecooled with a water bath
  2. customthe reaction was quenched by the addition of ice
  3. additionEtOAc was added
  4. customthe organic phase was separated
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customThe crude material was absorbed onto a plug of silica gel
  8. custompurified by chromatography
  9. washeluting with 3% to 5% EtOAc in hexane

Sources & evidence

ORD record
ord-bc54e24b545a43cab3b192a84742cb36
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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