2,2-Dimethyl-5-(1-methylethylidene)-1,3-dioxane-4,6-dione → HCID 118622760, compound

HRID 2202225Notes

Reaction equation

C([Mg]Cl)(C)C.[Br:6][C:7]1[CH:12]=[CH:11][C:10](I)=[C:9]([F:14])[CH:8]=1.[C:15](=[C:18]1[C:23](=[O:24])[O:22][C:21]([CH3:26])([CH3:25])[O:20][C:19]1=[O:27])([CH3:17])[CH3:16]>C1COCC1.C1(C)C=CC=CC=1>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:15]([CH:18]2[C:19](=[O:27])[O:20][C:21]([CH3:25])([CH3:26])[O:22][C:23]2=[O:24])([CH3:17])[CH3:16])=[C:9]([F:14])[CH:8]=1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution (183 mL, 182.79 mmol) of 1M isopropylmagnesium chloride in THF was added dropwise to a solution of 4-bromo-2-fluoro-1-iodobenzene (50.0 g, 166.17 mmol) in anhydrous THF (96 mL) over 20 min at −20° C. under argon atmosphere. The reaction mixture was stirred at −20° C. for 30 min, and added dropwise to a solution of 5-isopropylidene-2,2-dimethyl-1,3-dioxane-4,6-dione in anhydrous toluene (84 mL) over 20 min at −20° C., and then the used container was washed with THF (24 mL). The reaction mixture was stirred at 0° C. for 3 hr, 10% aqueous citric acid solution (200 mL) was added thereto at 0° C., and the mixture was extracted with toluene (200 mL). The organic layer was concentrated under reduced pressure to give 5-(2-(4-bromo-2-fluorophenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione as a pale-yellow oil.

Workup

washthe used container was washed with THF (24 mL)
stirringThe reaction mixture was stirred at 0° C. for 3 hr
addition10% aqueous citric acid solution (200 mL) was added
extractionat 0° C., and the mixture was extracted with toluene (200 mL)
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-63b395776f9e42fa9e00864cf2f96fb1
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365520B2

Reaction notes

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