Carbon Dioxide → 4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid

HRID 405695Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:25])[O:10][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH:12]=2)=[CH:4][C:3]=1[CH3:26].[Li]CCCC.[C:32](=[O:34])=[O:33].Cl>C1COCC1.CCCCCC.CCOCC>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([C:13]([F:16])([F:15])[F:14])[O:10][N:9]([CH3:25])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:32]([OH:34])=[O:33])=[C:3]([CH3:26])[CH:4]=3)=[CH:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

Conditions

Temperature: -90 °C

Procedure

210 mg of 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazole (IIIa) was dissolved in 20 ml of dry THF, cooled to −90° C. and treated with 0.625 ml BuLi 1.6M in hexane. The mixture was stirred for 1 hour at −80° C. and then a great excess of solid CO2 was added to the mixture. The temperature was allowed to rise up to −30° C. (1 hour) and 5 ml of 1M HCl was added followed with ether. The organic layer was dried and evaporated to dryness. The residual resin was used in the final step without purification.

Workup

customto rise up to −30° C.
additionwas added
customThe organic layer was dried
customevaporated to dryness
customwithout purification

Sources & evidence

ORD record: ord-4a29bd076f6c40468825e3149c213de9
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754053B2

Reaction notes

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