N-bromobutanimide → 2-Bromo-3-ethoxy-2-cyclohexen-1-one

Temperature

0 °C

To a solution of 3-ethoxy-2-cyclohexenone (70 g, 499 mmol) in CH2Cl2 (300 mL) as a solvent at 0° C. under argon atmosphere was added in portions N-bromosuccinimide (91 g, 511 mmol) over a period of 1 hour. The suspension was stirred at 0° C. for 1 hour and then at room temperature for 2 hours. The solvent was removed in vacuo and CH2Cl2 added. The solution was washed twice with a cold saturated NaHCO3 solution and with cold H2O, then dried over anhydrous MgSO4, the solvent removed in vacuo and the resulting solid residue was triturated several times with Et2O, the resulting solid dried in vacuo to afford 101 g (92% yield) of the desired product as white crystals which were characterized as follows:

1. waitat room temperature for 2 hours
2. customThe solvent was removed in vacuo and CH2Cl2
3. additionadded
4. washThe solution was washed twice with a cold saturated NaHCO3 solution and with cold H2O
5. dry with materialdried over anhydrous MgSO4
6. customthe solvent removed in vacuo
7. customthe resulting solid residue was triturated several times with Et2O
8. customthe resulting solid dried in vacuo

ORD record

ord-aa1be0e3b5a2460e9af6247269d7bf44

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07888338B2