Sodium Thiosulfate → 5-Bromo-4-cyclopropyl-3-fluoro-2-hydroxybenzaldehyde

HRID 2272520Notes

Reaction equation

HRID 2272520 reaction equation
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[CH:12]1([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[C:17]([OH:23])[C:16]=2[F:24])[CH2:14][CH2:13]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[Br:1][C:22]1[C:15]([CH:12]2[CH2:13][CH2:14]2)=[C:16]([F:24])[C:17]([OH:23])=[C:18]([CH:21]=1)[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 192912Dibromoisocyanuric acidHCID 904235724-Cyclopropyl-3-fluoro-2-hydroxybenzaldehyde

Product 1

HCID 904234915-Bromo-4-cyclopropyl-3-fluoro-2-hydroxybenzaldehydeYield 134%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dibromoisocyanuric acid (1.43 g) was added at room temperature to a DMF (50 mL) solution of 4-cyclopropyl-3-fluoro-2-hydroxybenzaldehyde (1.50 g), and the mixture was stirred at the same temperature as above for 3 hours in a nitrogen atmosphere. A saturated aqueous solution of sodium thiosulfate was added to the reaction mixture at room temperature, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (1.73 g)

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated saline in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0588c618ad6544ed9a671be368693346
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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