tert-Butyl acetate → Ethyl 2-(tert-butoxy)-2-(3,5-dibromothiophen-2-yl)acetate
Reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[CH:8]([OH:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl(O)(=O)(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(O[C:30]([CH3:33])([CH3:32])[CH3:31])(=O)C>>[C:30]([O:14][CH:8]([C:3]1[S:4][C:5]([Br:7])=[CH:6][C:2]=1[Br:1])[C:9]([O:11][CH2:12][CH3:13])=[O:10])([CH3:33])([CH3:32])[CH3:31]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Ethyl 2-(3,5-dibromothiophen-2-yl)-2-hydroxyacetate (10b) (160 mg, 0.47 mmol) was dissolved in tert-butyl acetate (8.7 mL) at −20° C. and 70% perchloric acid (1.1 mL) was rapidly added. The mixture was stirred at 0° C. for 3 hours then poured in a saturated solution of potassium carbonate. Layers were separated. The aqueous layer was extracted with ethyl acetate (2×20 mL). The organic layers were washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to provide the desired product (10c) (160 mg, 0.40 mmol, 86%).
Workup
- customLayers were separated
- extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
- washThe organic layers were washed with brine (10 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)
Sources & evidence
- ORD record
- ord-90ecaf58ac954883ab8cdb2495c54294
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238026B2
Reaction notes
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