Water → HCID 131732069, compound

HRID 339882Notes

Reaction equation

HRID 339882 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[S:15]([O-:18])([O-:17])=[O:16].[Na+:19].[Na+].O>CO>[Na+:19].[C:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:8][C:3]([CH2:2][S:15]([O-:18])(=[O:17])=[O:16])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24437Sodium SulfiteHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-

Product 1

HCID 131732069HCID 131732069, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 28.69 g of 4-bromomethylbiphenyl and 29.27 g of sodium sulfite in 200 ml of a mixture of water and methanol (1:1) was stirred at 60° C. for 12 hours. After cooling to room temperature, the solvent was removed under reduced pressure and the aqueous residue was extracted twice with 100 ml of ethyl acetate. The aqueous phase was concentrated by rotary evaporation and the solid residue was stirred with 200 ml of isopropanol for 1 hour. After filtration to remove the solid constituents, the filtrate was concentrated by rotary evaporation. This gave the product (15.80 g) with a molecular weight of 270.3 g/mol (C13H11O3S.Na).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under reduced pressure
  3. extractionthe aqueous residue was extracted twice with 100 ml of ethyl acetate
  4. concentrationThe aqueous phase was concentrated by rotary evaporation
  5. stirringthe solid residue was stirred with 200 ml of isopropanol for 1 hour
  6. filtrationAfter filtration
  7. customto remove the solid constituents
  8. concentrationthe filtrate was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-f8e9fec926c240e9815a893864dde942
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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