Potassium Hydroxide → 2-(2-Methoxy-phenylsulfanyl)-5-nitro-benzoic Acid

HRID 1825779Notes

Reaction equation

HRID 1825779 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].[OH-].[K+].Br[C:13]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]>O.[Cu]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:13]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 23642ThioguaiacolHCID 2430252-Bromo-5-nitrobenzoic acid

Product 1

HCID 221394572-(2-Methoxy-phenylsulfanyl)-5-nitro-benzoic AcidYield 104.8%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

2-Methoxythiophenol (9.9 ml, 81.29 mmol) was added to a solution of KOH (18.24 g, 325.18 mmol) in water (80 ml) degassed for 15 minutes. 2-Bromo-5-nitrobenzoic acid (20.0 g, 81.29 mmol) and copper bronze (258 mg, 4.06 mmol) were added to the reaction mixture, which was refluxed overnight. The reaction was stopped and the mixture was filtered through a celite pad and washed with 2M NaOH then water (50 ml). The filtrate was acidified (pH 1) with concentrated HCl. The precipitate formed was filtered and dried overnight in a vacuum oven (50° C.) to give the crude title compound (26.0 g) as a pale yellow solid. The product was used without further purification.

Workup

  1. customdegassed for 15 minutes
  2. temperaturewas refluxed overnight
  3. filtrationthe mixture was filtered through a celite pad
  4. washwashed with 2M NaOH
  5. customThe precipitate formed
  6. filtrationwas filtered
  7. customdried overnight in a vacuum oven (50° C.)

Sources & evidence

ORD record
ord-58eb7a6583904d82b3e85e771eb4d834
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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