Hydrochloric Acid → HCID 59833399, compound

HRID 1359955Notes

Reaction equation

HRID 1359955 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]=1

Participants

7

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

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. dry with materialthe solution was dried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under the reduced pressure
  5. 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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