Hydrochloric Acid → HCID 68459950, compound
Reaction equation
CO[C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2CC)=[CH:6][C:5]=1[Br:19].[CH3:21][CH:22](C[AlH]CC(C)C)C.Cl.CCOCC>C1(C)C=CC=CC=1>[Br:19][C:5]1[CH:6]=[C:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:21][CH3:22])=[CH:15][CH:16]=2)[CH:8]=[CH:9][C:4]=1[CH2:3][OH:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Under a nitrogen stream, to a solution of 2-bromo-4-(ethylphenoxy)-benzoic acid methyl ester (90 mg, 0.269 mmol) in anhydrous toluene (2 ml), a toluene solution of DIBAL (1M, 0.537 ml, 0.537 mmol) was added dropwise at −78° C. The reaction mixture was stirred at −78° C. for 1.5 hours and at room temperature for 1.5 hours. The reaction mixture was cooled again to −78° C., followed by addition of 1N hydrochloric acid (0.2 ml) and ether (3.5 ml). The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:5)) to give the titled compound (78 mg, 94%).
Workup
- temperatureThe reaction mixture was cooled again to −78° C.
- extractionThe reaction mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated aqueous sodium chloride
- dry with materialdried over sodium sulfate
- filtrationAfter filtration
- distillationthe solvent was distilled off under reduced pressure
- customthe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:5))
Sources & evidence
- ORD record
- ord-c7cc13c477ec4f0595a63bdcc37bdc31
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767651B2
Reaction notes
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