Acetone → 1-Acetyl-6-bromospiro[indoline-3,3'-thietane]1',1'-dioxide

HRID 1618786Notes

Reaction equation

HRID 1618786 reaction equation
[C:1]([N:4]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:16])[CH:14]=2)[C:6]2([CH2:9]S[CH2:7]2)[CH2:5]1)(=[O:3])[CH3:2].CO.CC(C)=O.O[O:24][S:25]([O-:27])=O.[K+]>O>[C:1]([N:4]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:16])[CH:14]=2)[C:6]2([CH2:9][S:25](=[O:27])(=[O:24])[CH2:7]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 582217341-Acetyl-6-bromo-1,2-dihydrospiro[indole-3,3'-thietane]

Product 1

HCID 582214181-Acetyl-6-bromospiro[indoline-3,3'-thietane]1',1'-dioxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred ice-cooled solution of 1-acetyl-6-bromo-1,2-dihydrospiro[indole-3,3′-thietane] (0.288 g, 0.97 mmol) in a mixture water (2.4 mL), MeOH (18.9 mL), and acetone (4.7 mL) was added a solution of oxone (1.19 g, 1.93 mmol) in water (1.8 mL). The ice bath was removed and the solution was stirred at rt for 4 h. The mixture was poured into saturated aqueous ammonium chloride and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo to give 1-acetyl-6-bromo-1,2-dihydrospiro[indole-3,3′thietane]1′,1′-dioxide as a tan solid. Mass Spectrum (ESI) m/e=330.0 [(M+1) (79Br)] and 332.0 [(M+1) (81Br)].

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was poured into saturated aqueous ammonium chloride
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-22639a57e04a4a389f6b63af1fc9c7db
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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