Carbon Dioxide → HCID 22475029, compound

HRID 2103123Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

To a cooled (-78° C.) solution of 5-bromo-2-(2,4-dichloro-phenyl)-6-fluoro-2-(4-fluoro-phenyl)-benzo[1,3]dioxole (16.5 g, 36.0 mmol) in diethyl ether (250 mL) was slowly added a solution of n-butyl lithium in hexanes (1.6M, 23 mL, 36.0 mmol, 1.0 eq.). After 1 h at −78° C., solid carbon dioxide (50 g approx.) was added to the solution and the reaction was allowed to warm up to 20° C. After 16 h at 20° C. the reaction mixture was partitioned between water (150 mL), ethyl acetate (1.5 L) and hydrochloric acid (1N, 150 mL). The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water. The volatiles were removed in vacuo. Purification by flash chromatography afforded the title compound (10.73 g, 69%) as a light yellow solid.

Workup

customAfter 16 h at 20° C. the reaction mixture was partitioned between water (150 mL), ethyl acetate (1.5 L) and hydrochloric acid (1N, 150 mL)
extractionThe aqueous layer was extracted with ethyl acetate
washthe combined organic layers were washed with water
customThe volatiles were removed in vacuo
customPurification by flash chromatography

Sources & evidence

ORD record: ord-0bebc0ca9bf64c738e67c26f630074aa
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576088B2

Reaction notes

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