Perchloric Acid → HCID 70855555, compound

HRID 591039Notes

Reaction equation

HRID 591039 reaction equation
Cl(O)(=O)(=O)=O.[Br:6][C:7]1[C:8]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:9]=2[S:10][C:11]=1[CH:12]([OH:17])[C:13]([O:15][CH3:16])=[O:14]>C(OC(C)(C)C)(=O)C>[Br:6][C:7]1[C:8]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:9]=2[S:10][C:11]=1[CH:12]([O:17][C:8]([CH3:21])([CH3:9])[CH3:7])[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 70855549HCID 70855549, compound

Product 1

HCID 70855555HCID 70855555, compoundYield 149.4%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

Under a nitrogen atmosphere, perchloric acid (70%, 1.33 mL) was added at −10° C. to a solution of methyl (3-bromo-4-methyl-benzo[b]thiophen-2-yl)-hydroxy-acetate (23h) (250 mg, 0.79 mmol) in tert-butyl acetate (10 mL). After 1 hour, the reaction was quenched with a saturated aqueous solution of sodium bicarbonate and extracted with dichloromethane (2×30 mL). The organic layer was washed with brine (20 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired product (23i) as a white solid (220 mg, 0.59 mmol, 75%).

Workup

  1. customthe reaction was quenched with a saturated aqueous solution of sodium bicarbonate
  2. extractionextracted with dichloromethane (2×30 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-15227b860f074c65bafd6ae8135cd30a
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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