Dimethylformamide → N,N-Diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[O:3]1.CN(C=O)C.[H-].[Na+].I[CH2:25][CH3:26].[CH3:27][CH2:28]OC(C)=O>>[CH2:27]([N:15]([CH2:25][CH3:26])[C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1)[CH3:28]Participants
6
Procedure
4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (500 mg, 2.28 mmol, 1 eq.) is dissolved in anhyd. DMF (5 mL) and cooled to 0° C. NaH (60% dispersion, 201 mg, 5.02 mmol, 2.2 eq.) is added and the resulting mixture is stirred at 0° C. for 30 min after which iodoethane (0.38 mL, 2.1 eq) is added dropwise to the reaction mixture. Once this addition is complete, the reaction mixture is allowed to warm to room temperature and stir for 3 days. The reaction is diluted with EtOAc and sequentially washed with H2O (5×) and saturated aqueous NaCl. The organic solution is dried over Na2SO4 and concentrated to give Diethyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine as a sticky tan solid: ESMS m/z 276.1 (M+H+).
Workup
- additionis added dropwise to the reaction mixture
- additionOnce this addition
- washsequentially washed with H2O (5×) and saturated aqueous NaCl
- dry with materialThe organic solution is dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-71330d99b58c4ad880a8a9da4c097be1
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153671B2
Reaction notes
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