Sodium Thiosulfate → 4-Bromo-5-fluoro-2-methylaniline

HRID 34125

Reaction equation

HRID 34125 reaction equation
[F:1][C:2]1[CH:8]=[C:6]([NH2:7])[C:5]([CH3:9])=[CH:4][CH:3]=1.[Br:10]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Br:10][C:3]1[C:2]([F:1])=[CH:8][C:6]([NH2:7])=[C:5]([CH3:9])[CH:4]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 677745-Fluoro-o-toluidine

Product 1

HCID 70180444-Bromo-5-fluoro-2-methylanilineYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 49.0 g of 5-fluoro-o-toluidine in 600 mL of dichloromethane was added 69.7 g of N-bromosuccinimide at 0° C., and stirred at this temperature for an hour. Then sodium thiosulfate aqueous solution was added, and the reaction solution was evaporated and diluted with ethyl acetate. The organic layer was washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. Then the solvent was evaporated, and the precipitated crystals were washed with diethyl ether:n-hexane=1:10, to afford 81.6 g of the title compound as colorless crystals.

Workup

  1. customthe reaction solution was evaporated
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThen the solvent was evaporated
  6. washthe precipitated crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-569024928a0c4303b8725395bd1d2d18
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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