Hydrochloric Acid → HCID 59833399, compound
Reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15])(=O)C.[OH-].[Na+].[Cl-].[NH4+].Cl>CO.C(OCC)(=O)C>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][OH:4])=[C:8]([N+:14]([O-:16])=[O:15])[CH:9]=1Participants
Procedure
4-Bromo-2-nitrophenethyl acetate (270 mg, 0.96 mmol) was dissolved in 4 ml of methanol. A 5 N aqueous NaOH solution (0.97 ml, 4.82 mmol) was added to the solution at room temperature with stirring, and the mixture was stirred at room temperature for 2 hr. A 10% aqueous ammonium chloride solution (5 ml) was added to the reaction solution, and the mixture was neutralized with a 1 N aqueous HCl solution. The resultant precipitate was dissolved in 20 ml of ethyl acetate, and the solution was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to give 198 mg (yield 83%) of the title compound.
Workup
- stirringthe mixture was stirred at room temperature for 2 hr
- dry with materialthe solution was dried over anhydrous sodium sulfate
- filtrationAfter filtration
- concentrationthe filtrate was concentrated under the reduced pressure
- customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1)
Sources & evidence
- ORD record
- ord-145fadc8dbd24e74a4e9eb5ed1ed171c
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879808B2
Reaction notes
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