1-Butanol → HCID 86703756, compound
Reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:12][C:13]1[C:14](F)=[CH:15][C:16]([F:26])=[C:17]([CH:25]=1)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].Cl>CS(C)=O>[CH2:1]([O:5][C:14]1[C:13]([Cl:12])=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])=[C:16]([F:26])[CH:15]=1)[CH2:2][CH2:3][CH3:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of butanol (0.07 g, 0.99 mmol) in anhydrous dimethylsulfoxide (2 mL) were added cesium carbonate (0.59 g, 1.81 mmol) and tert-butyl 5-chloro-2,4-difluorobenzoate (0.22 g, 0.90 mmol) and the reaction mixture was stirred at 70° C. for 16 hours. The reaction mixture was cooled down to room temperature and acidified to pH=1 with 5% aqueous hydrochloric acid solution and extracted with ethyl acetate (2×15 mL). The combined organic layers were washed with brine (15 mL); dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by column chromatography (0 to 10% ethyl acetate in hexanes) afforded the title compound (0.23 g, 72%); MS (ES+) m/z 303.2, 305.2 (M+1).
Workup
- temperatureThe reaction mixture was cooled down to room temperature
- extractionextracted with ethyl acetate (2×15 mL)
- washThe combined organic layers were washed with brine (15 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification of the residue by column chromatography (0 to 10% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-a1ba06972b6f4f308fd49aa3ac9c1345
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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