Sodium hydride → 3-Methyl-2-(trifluoromethylsulfonyloxy)benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1)[OH:6].[H-].[Na+].[F:15][C:16]([S:19](O)(=[O:21])=[O:20])([F:18])[F:17]>ClCCl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=1[O:6][S:19]([C:16]([F:18])([F:17])[F:15])(=[O:21])=[O:20]Participants
Conditions
- Temperature
- 0 °C
Procedure
In an inert atmosphere, a stirred solution of 3-methylsalicylic acid methyl ester (9.96 g) in dichloromethane (150 mL) cooled in an ice bath, was treated portionwise with 55% sodium hydride dispersion in mineral oil (3.0 g). The mixture was stirred at 0° C. for 15 minutes, then trifluoromethyl sulfonic acid (18.65 mL) was added dropwise over 20 minutes. The cooling bath was removed and the reaction was allowed to proceed for an additional hour. Water (75 mL) was added and the phases were separated. The organic layer was washed in turn with 10% potassium carbonate (75 mL) and with brine. The dried (Na2SO4) organic layer was evaporated and the resulting amber oil was purified by HPLC (diethyl ether-hexane; 1:4) to yield 14.3 g of 3-methyl-2-(trifluoromethylsulfonyloxy)benzoic acid methyl ester as an oil.
Workup
- customThe cooling bath was removed
- waitto proceed for an additional hour
- additionWater (75 mL) was added
- customthe phases were separated
- washThe organic layer was washed in turn with 10% potassium carbonate (75 mL) and with brine
- dry with materialThe dried (Na2SO4) organic layer
- customwas evaporated
- customthe resulting amber oil was purified by HPLC (diethyl ether-hexane; 1:4)
Sources & evidence
- ORD record
- ord-35cb26d6b80a4356a6092a1ac2696fb9
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344843
Reaction notes
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