Diethyl Ether → HCID 59648113, compound
Reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][CH2:11][C:12]1[CH:16]=[C:15]([CH3:17])[O:14][N:13]=1.CCOCC>CN(C=O)C>[Br:1][C:16]1[C:12]([CH2:11][O:10][CH3:9])=[N:13][O:14][C:15]=1[CH3:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
N-bromosuccinimide (590 mg, 3.31 mmol) was added to 3-methoxymethyl-5-methyisoxazole (351 mg, 2.76 mmol) in DMF (3.5 mL) at room temperature under nitrogen. The reaction was heated at 60° C. for 15 h then allowed to cool to room temperature. Ether (50 mL) was added to the reaction mixture, then washed with water (3×10 mL), saturated aqueous sodium hydrogen carbonate (10 mL), and brine (10 mL). The organic layer was dried over magnesium sulfate, filtered, and evaporated to provide 526 mg (92% yield) of 4-bromo-3-methoxymethyl-5-methylisoxazole as a clear liquid which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) δ ppm 4.50 (s, 2H), 3.41 (s, 3H), 2.43 (s, 3H).
Workup
- temperatureto cool to room temperature
- washwashed with water (3×10 mL), saturated aqueous sodium hydrogen carbonate (10 mL), and brine (10 mL)
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-bdf4a762c30a4b41bfe94f1966e154a7
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884107B2
Reaction notes
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