Methyl iodide → 6-[2-(4-Bromo-2-chloro-phenyl)-propionyl]-3-methyl-3H-benzooxazol-2-one

HRID 2096832Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:21]=[CH:20][C:14]3[N:15]([CH3:19])[C:16](=[O:18])[O:17][C:13]=3[CH:12]=2)=[O:10])=[C:4]([Cl:22])[CH:3]=1.[H-].[Na+].[CH3:25]I>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:25])[C:9]([C:11]2[CH:21]=[CH:20][C:14]3[N:15]([CH3:19])[C:16](=[O:18])[O:17][C:13]=3[CH:12]=2)=[O:10])=[C:4]([Cl:22])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-[2-(4-Bromo-2-chloro-phenyl)-acetyl]-3-methyl-3H-benzooxazol-2-one (747 mg) was dissolved in DMF (20 mL). The mixture was cooled to 0° C. To this solution was added sodium hydride (55% in mineral oil, 90 mg). The mixture was stirred for 10 minutes at 0° C. and then for 1 hour at r.t. The mixture was cooled to 0° C. and methyl iodide (292 mg) was added dropwise over a period of 10 minutes. Stirring was continued over night at r.t. The reaction mixture was poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a brown foam (531 mg, 69%). MS (neg. ion, m/e)=394.2 [M−H)−].

Workup

waitfor 1 hour at r.t
temperatureThe mixture was cooled to 0° C.
stirringStirring
waitwas continued over night at r.t
extractionextracted two times with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent was evaporated
customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record: ord-81bc0af71459441285d64d8497c98dfc
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450313B2

Reaction notes

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