Hydrogen Bromide → HCID 24782635, compound

HRID 1685804Notes

Reaction equation

HRID 1685804 reaction equation
[C:1]([C:3]1([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:21])[C:17]([O:19]C)=[O:18])=[CH:12][CH:11]=2)[C:7](=[O:8])[CH2:6][S:5][CH2:4]1)#[N:2].Br>O1CCOCC1>[C:1]([C:3]1([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH3:21])[C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)[C:7](=[O:8])[CH2:6][S:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 24782634HCID 24782634, compound

Product 1

HCID 24782635HCID 24782635, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-[4-(3-cyano-4-oxothiolan-3-ylmethyl)phenyl]propionate (2.0 g) obtained in Example 6 was dissolved in 1,4-dioxane (14 ml), then, 47% aqueous hydrobromic acid (10.0 ml) was added and stirred overnight at room temperature. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (1.36 g, 78%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-c155b6ed398247108370f608ce10d75a
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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