Sodium Thiosulfate → (4-Bromo-3-methoxyphenyl)-methanol

HRID 1662771Notes

Reaction equation

HRID 1662771 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].S([O-])(O)=O.[Na+].[Br:16]([O-])(=O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC#N.O.CCOCC>[Br:16][C:10]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 814373-Methoxybenzyl alcoholHCID 23665763Sodium BisulfiteHCID 23668195Sodium Bromate

Product 1

HCID 13551345(4-Bromo-3-methoxyphenyl)-methanolYield 63.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of 5.00 g of 3-methoxybenzyl alcohol in MeCN-water (180 ml, 1:1) was added 8.60 g sodium hydrogen sulfite and 8.19 g of sodium bromate and the reaction mixture was stirred at room temperature for two hours. After the reaction, an aqueous solution of 10% sodium thiosulfate and Et2O were added, and liquid separation was performed. After the organic layer was sequentially washed with 5% K2CO3, water and saturated brine, and dried over MgSO4, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/4; v/v) to obtain 5.02 g of the title compound (colorless solid).

Workup

  1. customAfter the reaction
  2. customliquid separation
  3. washAfter the organic layer was sequentially washed with 5% K2CO3, water and saturated brine
  4. dry with materialdried over MgSO4
  5. customthe drying agent was separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/4; v/v)

Sources & evidence

ORD record
ord-ec3515e3343644248e698ea0ba09d04a
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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