Cesium carbonate → 3-Iodo-5-methanesulfonyl-phenol

HRID 418064Notes

Reaction equation

C1C=CC(/C=N\O)=CC=1.[C:10](=[O:13])([O-])[O-].[Cs+].[Cs+].[I:16][C:17]1[CH:22]=C([N+]([O-])=O)[CH:20]=[C:19]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:18]=1>CN(C=O)C.CCOC(C)=O>[I:16][C:17]1[CH:22]=[C:10]([OH:13])[CH:20]=[C:19]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:18]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of syn-benzaldehyde oxime (3.71 g, 30.6 mmol) in DMF (80 mL) was added cesium carbonate (19.9 g, 61.3 mmol) and heated to 90° C. for 1-2 min before a solution of 1-iodo-3-methanesulfonyl-5-nitro-benzene (5.0 g, 15.3 mmol) in DMF (80 mL) was added. The resulting dark brown solution was stirred at 90° C. for 15 h. The reaction mixture was then cooled down and diluted with EtOAc and washed with 10% HCl. The organic phase was then washed again with brine. The combined organic extracts were dried over sodium sulfate and evaporated under reduced pressure to obtain a crude brown oil which was purified on ISCO column (330 g). The desired compound was eluted with 70% EtOAc-Hexanes. The desired fractions were combined and evaporated under reduced pressure to afford 2.5 g (55%) of 3-iodo-5-methanesulfonyl-phenol as an orange solid. HR-ES(+) m/e calcd for C7H7O3SI (M+H)+ 298.9234, found 298.9234.

Workup

additionwas added
temperatureThe reaction mixture was then cooled down
washwashed with 10% HCl
washThe organic phase was then washed again with brine
dry with materialThe combined organic extracts were dried over sodium sulfate
customevaporated under reduced pressure
customto obtain a crude brown oil which
customwas purified on ISCO column (330 g)
washThe desired compound was eluted with 70% EtOAc-Hexanes
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-1cb235526fba460f86844677a2254a6e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093253B2

Reaction notes

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