Potassium Carbonate → HCID 59138598, compound

HRID 1514074Notes

Reaction equation

HRID 1514074 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]([CH3:21])[CH3:20].C([O-])([O-])=O.[K+].[K+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:16][O:17][C:18](=[O:22])[C:19]([CH3:21])([CH3:20])[CH:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 9817365HCID 9817365, compound

Product 1

HCID 59138598HCID 59138598, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (5-bromo-thiophen-2-yl)-(3-fluoro-phenyl)-methanol (3.40 mmol) and (1-methoxy-2-methyl-propenyloxy)-trimethyl-silane (3.45 ml, 17 mmol) in dichloromethane (10 ml) at 0° C. was added a solution of titanium tetrachloride in dichloromethane (1M solution, 7.4 ml, 7.4 mmol) slowly. After being stirred at 0° C. for 10 minutes and room temperature for 3 hours, the reaction mixture was poured onto an iced aqueous K2CO3. The solution was extracted with dichloromethane. The organic layer was washed, dried (MgSO4) and concentrated to give 3-(5-bromo-thiophen-2-yl)-3-(3-fluoro-phenyl)-2,2-dimethyl-propionic acid methyl ester as a viscous yellow oil (1.104 g, 87.5% yield). LC/MS (m/z) 393.13 [(M+23)+]; HPLC Rt: 3.883 min.

Workup

  1. extractionThe solution was extracted with dichloromethane
  2. washThe organic layer was washed
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab31a0d74e494d538aac29d2a4b4ac2d
Source dataset
uspto-grants-2012_07
Patent number
US08222247B2

Reaction notes

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