Benzyl Bromide → Benzyl 2-(benzyloxy)-4-chlorobenzoate
Reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C.CCOCC.O>[CH2:18]([O:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1)=[O:5])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
7
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 7.0 g (40.6 mmol) 2-hydroxy-4-chlorobenzoic acid in 150 ml of dry DMF was added 16.8 g (122 mmol) of K2CO3 followed by the dropwise addition of 15.2 g (89.2 mmol) of benzyl bromide. The reaction mixture was warmed to 50° C. and stirred overnight. After 16h, the reaction mixture was diluted with Et2O and H2O and the layers were separated. The aqueous layer was extracted with Et2O (2×) and the combined organic layers were successively washed with 1N HCl (3×100 ml), saturated NaHCO3 solution (2×50 ml) and brine (1×50 ml). The solution was dried over anhydrous MgSO4 and concentrated to give 2-benzyloxy-4-chlorobenzoic acid, benzyl ester as a pale yellow solid which was used without further purification.
Workup
- customthe layers were separated
- extractionThe aqueous layer was extracted with Et2O (2×)
- washthe combined organic layers were successively washed with 1N HCl (3×100 ml), saturated NaHCO3 solution (2×50 ml) and brine (1×50 ml)
- dry with materialThe solution was dried over anhydrous MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bd88343255c74ef5b3b06cc08fe14034
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403584B1
Reaction notes
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