Boron tribromide → 4-{2-[4-(3,3-Dimethyl-butyl)-piperazin-1-yl]-2-oxo-ethoxy}-3-methyl-benzoic Acid
Reaction equation
B(Br)(Br)Br.C[O:6][C:7](=[O:31])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:20][CH2:19]2)=[O:17])=[C:10]([CH3:30])[CH:9]=1>ClCCl>[CH3:27][C:26]([CH3:29])([CH3:28])[CH2:25][CH2:24][N:21]1[CH2:20][CH2:19][N:18]([C:16](=[O:17])[CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([C:7]([OH:31])=[O:6])=[CH:9][C:10]=2[CH3:30])[CH2:23][CH2:22]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1M Boron tribromide solution (2.66 ml, 2.66 mmol) was added dropwise to a solution of 4-{2-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-2-oxo-ethoxy}-3-methyl-benzoic acid methyl ester from Example E41.3 (500 mg, 1.33 mmol) in dichloromethane (20 ml) at 0° C. under an inert atmosphere. The mixture was stirred for 20 h at room temperature then cooled down to 0° C. 1M Boron tribromide solution (1.33 ml, 1.33 mmol) was added and the mixture was stirred for 2 h at room temperature. Solvents were re-moved in vacuo and azeotroped with toluene. The residue was purified by flash chromatography on silica gel (eluant; 1% acetic acid:5% methanol:94% chloroform) to yield the title compound (350 mg, 72%).
Workup
- temperaturethen cooled down to 0° C
- stirringthe mixture was stirred for 2 h at room temperature
- customazeotroped with toluene
- customThe residue was purified by flash chromatography on silica gel (eluant; 1% acetic acid:5% methanol:94% chloroform)
Sources & evidence
- ORD record
- ord-32953edacc2048c398486d59d17182ee
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202858B2
Reaction notes
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