Sodium Thiosulfate → Benzoic acid, 4-(bromomethyl)-3-fluoro-, ethyl ester

HRID 1257459Notes

Reaction equation

HRID 1257459 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:14]N1C(=O)CCC1=O.N(C(CC)C#N)=NC(CC)C#N.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C>[Br:14][CH2:13][C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 130802432,2''-AzobisbutyronitrileHCID 13489923Benzoic acid, 3-fluoro-4-methyl-, ethyl ester

Product 1

HCID 13489924Benzoic acid, 4-(bromomethyl)-3-fluoro-, ethyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution (11 ml) of the compound (2.0 g, 11 mmol) obtained in Example 189a in ethyl acetate were added N-bromosuccinimide (2.9 g, 17 mmol) and 2,2′-azobisbutyronitrile (AIBN) (180 mg, 1.1 mmol), and the mixture was heated under reflux for 5 hr under light irradiation. An aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=90/10) to give a crude title compound (2.3 g, 81%) as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hr under light irradiation
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by column chromatography (hexane-hexane/ethyl acetate=90/10)

Sources & evidence

ORD record
ord-0f12852106434b029e25ed479c2aacd6
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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