Potassium Carbonate → HCID 59138568, compound

HRID 1514079Notes

Reaction equation

[Br:1][C:2]1[S:6][C:5]([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)O)=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]([O:22][Si](C)(C)C)=[C:19](C)[CH3:20].C([O-])([O-])=O.[K+].[K+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH:19]([CH3:20])[C:18]([O:17][CH3:16])=[O:22])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (5-bromo-thiophen-2-yl)-(3-fluoro-phenyl)-methanol (2 g, 6.96 mmol) and (1-methoxy-2-methyl-propenyloxy)-trimethyl-silane (2.23 g, 13.92 mmol) in dichloromethane (20 ml) at 0° C. was added a solution of titanium tetrachloride in dichloromethane (1M solution, 7.7 ml, 7.66 mmol) slowly. After being stirred at 0° C. for 10 minutes and room temperature overnight, the reaction mixture was poured into an iced aqueous solution of K2CO3. The solution was extracted with dichloromethane. The organic layer was washed, dried (MgSO4) and concentrated to give the crude product. The crude product was purified by silica gel flash chromatography using 10% ethyl acetate in hexanes to give methyl 3-(5-bromothiophen-2-yl)-3-(3-fluorophenyl)-2-methyl-propanoate as a viscous yellow oil (1.74 g, 70% yield). HPLC Rt: 3.97 min.

Workup

extractionThe solution was extracted with dichloromethane
washThe organic layer was washed
dry with materialdried (MgSO4)
concentrationconcentrated
customto give the crude product
customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-661c9def68b84fa4aa5bc946d05beb3b
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222247B2

Reaction notes

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