Water → HCID 22614273, compound
Reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:17])=[C:5]([CH:10]=[CH:11][C:12]=1[S:13]([CH3:16])(=[O:15])=[O:14])[C:6]([O:8]C)=[O:7].CC(C)([O-])C.O.[OH-].[Na+].[CH:26]1([OH:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>>[Cl:17][C:4]1[C:3]([CH2:2][O:32][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]Participants
6
Procedure
1.0 g (2.93 mmol) of methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate was dissolved in 10 ml of cyclohexanol and treated with 0.33 g (2.93 mmol) of potasisum tert-butoxide. The mixture was stirred overnight at room temperature and then concentrated on a rotary evaporator. The residue was dissolved in 16 ml of tetrahydrofuran and 8 ml of water and refluxed for 4 h together with 0.55 g of NaOH (13.74 mmol). It was then allowed to cool and was largely concentrated on a rotary evaporator and the aqueous residue was then treated with 2 M HCl. It was then extracted with methylene chloride, and the combined organic phase was dried over MgSO4 and completely concentrated on a rotary evaporator.
Workup
- concentrationconcentrated on a rotary evaporator
- dissolutionThe residue was dissolved in 16 ml of tetrahydrofuran
- temperatureto cool
- concentrationwas largely concentrated on a rotary evaporator
- additionthe aqueous residue was then treated with 2 M HCl
- extractionIt was then extracted with methylene chloride
- dry with materialthe combined organic phase was dried over MgSO4
- concentrationcompletely concentrated on a rotary evaporator
Sources & evidence
- ORD record
- ord-619f143379bb4adca1609cbdc8fd8355
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06376429B1
Reaction notes
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