Hydrochloric Acid → 4-Borono-3-(2-m-tolyl-ethoxy)-benzoic Acid Methyl Ester
Reaction equation
CN(C)CCOCCN(C)C.C([Mg]Cl)(C)C.[CH3:17][O:18][C:19](=[O:37])[C:20]1[CH:25]=[CH:24][C:23](I)=[C:22]([O:27][CH2:28][CH2:29][C:30]2[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=2)[CH:21]=1.[B:38](OC)([O:41]C)[O:39]C.Cl>C1COCC1>[CH3:17][O:18][C:19](=[O:37])[C:20]1[CH:25]=[CH:24][C:23]([B:38]([OH:41])[OH:39])=[C:22]([O:27][CH2:28][CH2:29][C:30]2[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=2)[CH:21]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
2.3 g of bis(2-dimethylaminoethyl)ether were dissolved in 50 ml of anhydrous THF and 7.1 ml of a 2 M solution of isopropylmagnesium chloride added at 15° C. The mixture was stirred for 20 min at 15° C. Then a solution of 4.7 g of 4-iodo-3-(2-m-tolyl-ethoxy)-benzoic acid methyl ester in 20 ml of anhydrous THF was added at room temperature. The mixture was stirred for 10 min at 20° C., and then 2.4 g of trimethyl borate were added dropwise at 0° C. and the mixture stirred for 20 min at 0° C. 100 ml of 0.1 N hydrochloric acid were added, and the mixture was extracted three times with 100 ml of EA. The combined organic layers were washed with 100 ml of water, dried with magnesium sulfate and evaporated. Silica gel chromatography (EA/HEP 1:5) of the residue yielded 2.1 g of the title compound.
Workup
- stirringThe mixture was stirred for 10 min at 20° C.
- stirringthe mixture stirred for 20 min at 0° C
- extractionthe mixture was extracted three times with 100 ml of EA
- washThe combined organic layers were washed with 100 ml of water
- dry with materialdried with magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-44b70de1b28444469d191317f0a809fd
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618304B2
Reaction notes
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