Hydrogen Bromide → HCID 21998080, compound

HRID 1977440Notes

Reaction equation

HRID 1977440 reaction equation
Br.[C:2]([O:7][CH2:8][C:9]1[CH:14]=[C:13]([O:15][Si](C(C)(C)C)(C)C)[CH:12]=[C:11]([O:23][Si](C(C)(C)C)(C)C)[CH:10]=1)(=[O:6])[C:3]([CH3:5])=[CH2:4].[F-].[K+].Cl>C(#N)C.ClCCl>[C:2]([O:7][CH2:8][C:9]1[CH:10]=[C:11]([OH:23])[CH:12]=[C:13]([OH:15])[CH:14]=1)(=[O:6])[C:3]([CH3:5])=[CH2:4]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 522689Potassium FluorideHCID 54082292HCID 54082292, compound

Product 1

HCID 21998080HCID 21998080, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Concentrated hydrobromic acid (48%, 2.25 ml) was added dropwise to 3,5-di-tert-butyldimethylsilyloxybenzyl methacrylate (15.0 g, 34.4 mmole) and anhydrous potassium fluoride (7.5 g, 129 mmole) in acetonitrile (75 ml). After the solution was stirred overnight at room temperature, hydrochloric acid (4.5 ml conc. HCl in 30 ml of water) and 75 ml of dichloromethane were added to the pink solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with water and brine. The solution was dried twice over sodium sulfate, filtered over silica and after addition of toluene concentrated in vacuo. The oily residue was dissolved in isopropyl ether (38 ml) and precipitated in hexane (500 ml). The product was filtered off and recrystallized from isopropyl ether/hexane.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washwashed with water and brine
  4. dry with materialThe solution was dried twice over sodium sulfate
  5. filtrationfiltered over silica
  6. additionafter addition of toluene
  7. concentrationconcentrated in vacuo
  8. dissolutionThe oily residue was dissolved in isopropyl ether (38 ml)
  9. customprecipitated in hexane (500 ml)
  10. filtrationThe product was filtered off
  11. customrecrystallized from isopropyl ether/hexane

Sources & evidence

ORD record
ord-81bd1605a2df4c358751f8bb9b45c1fa
Source dataset
uspto-grants-2001_05
Patent number
US06232430B1

Reaction notes

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