tert-Butanol → tert-Butyl 2-(bromomethyl)-6-methylbenzoate
Reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:4]=1[C:5](Br)=[O:6].[C:13]([OH:17])([CH3:16])([CH3:15])[CH3:14]>CCCCCCC>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:4]=1[C:5]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
20 g (24 mmol) of 2-bromomethyl-6-methylbenzoyl bromide solution (35% solution in heptane) are added to a mixture of 15 ml of n-heptane and 25 ml of tert-butanol. After stirring at 40° C. for one hour, 400 ml of n-heptane are added. The solution is washed successively with 60 ml of sat. sodium hydrogencarbonate solution and washed four times with 20 ml each time of water. Subsequently, the solvent is removed fully under reduced pressure. When the conversion is quantitative, tert-butyl 2-bromomethyl-6-methylbenzoate is obtained as a virtually colorless oil having 93% purity and having a molecular weight of 284.04 (C13H17BrO2); MS (ESI): 302.1 [M+NH4]+.
Workup
- washThe solution is washed successively with 60 ml of sat. sodium hydrogencarbonate solution
- washwashed four times with 20 ml each time of water
- customSubsequently, the solvent is removed fully under reduced pressure
Sources & evidence
- ORD record
- ord-56abdecf30c745ee973a7d6dfd83975e
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07803950B2
Reaction notes
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