Perchloric Acid → HCID 86717840, compound

HRID 591031Notes

Reaction equation

HRID 591031 reaction equation
Cl(O)(=O)(=O)=O.[Br:6][C:7]1[C:8]2[CH:21]=[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[CH:21]=[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 86717838HCID 86717838, compound

Product 1

HCID 86717840HCID 86717840, compoundYield 150.5%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

Under a nitrogen atmosphere, perchloric acid (70%, 1.9 mL) was added at −10° C. to a solution of methyl (3-bromo-benzo[b]thiophen-2-yl)-hydroxy-acetate (21c) (560 mg, 1.86 mmol) in tertbutyl acetate (15 mL). After 1 hour, the reaction was quenched with a saturated solution of sodium carbonate 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 95/5) to afford the desired product (21d) as a yellow oil (500 mg, 1.40 mmol, 75%).

Workup

  1. customthe reaction was quenched with a saturated solution of sodium carbonate
  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 95/5)

Sources & evidence

ORD record
ord-91b6e3ceb825493786b1b1cc0c89d02b
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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