Benzoyl Peroxide → Ethyl 2-bromomethyl-6-methoxybenzoate
Reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[C:30]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:40][C:36]1[CH:37]=[CH:38][CH:39]=[C:29]([O:28][CH3:27])[C:30]=1[C:31]([O:33][CH2:34][CH3:35])=[O:32]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
19.56 g of N-bromosuccinimide and 4.84 g of benzoyl peroxide were added to a solution of 19.40 g of ethyl 2-methoxy-6-methylbenzoate in 150 ml of carbon tetrachloride. The reaction medium was refluxed for 6 hours (no further change). The reaction medium was cooled to 5° C. and the succinimide was filtered. The organic phase was washed with a saturated sodium hydrogen carbonate solution (2×150 ml), dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel (column puriFlash, IR-50SI/800G, Spot II) eluted with heptane/ethyl acetate (gradient). 15.5 g of ethyl 2-bromomethyl-6-methoxybenzoate were obtained in the form of a yellow oil which later crystallizes. Yield=56%.
Workup
- temperatureThe reaction medium was refluxed for 6 hours (no further change)
- filtrationthe succinimide was filtered
- washThe organic phase was washed with a saturated sodium hydrogen carbonate solution (2×150 ml)
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue was purified by chromatography on silica gel (column puriFlash, IR-50SI/800G, Spot II)
- washeluted with heptane/ethyl acetate (gradient)
Sources & evidence
- ORD record
- ord-4c934444938843a984b7dccc6f7c2ba9
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090596B2
Reaction notes
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