Sodium Sulfite → Sodium (4-fluoro-3-phenoxyphenyl)methanesulfonate

HRID 479885Notes

Reaction equation

HRID 479885 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=1.[S:17]([O-:20])([O-:19])=[O:18].[Na+:21].[Na+]>CO>[F:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][S:17]([O-:20])(=[O:19])=[O:18])=[CH:4][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na+:21]

Participants

4

Reactant 2

HCID 24437Sodium SulfiteHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzene

Product 1

HCID 86757418Sodium (4-fluoro-3-phenoxyphenyl)methanesulfonateYield 64.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of α-bromo-4-fluoro-3-phenoxytoluene (4.86 g, 17.3 mmol) and sodium sulfite (2.39 g, 19 mmol) in 50% aqueous methanol (20 ml) is heated at reflux for 5 hours and cooled to room temperature. The resultant colorless solid is collected by filtration and washed with chilled 50% aqueous methanol and methanol to obtain 3.4 g of sodium (4-fluoro-3-phenoxyphenyl)methanesulfonate. Another 1.8 g of product is recovered from the mother liquors.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 5 hours
  3. filtrationThe resultant colorless solid is collected by filtration
  4. washwashed
  5. temperaturewith chilled 50% aqueous methanol and methanol

Sources & evidence

ORD record
ord-6110e9f3eefd4fe8980d63fdf3d7dbbd
Source dataset
uspto-grants-2003_11
Patent number
US06646166B1

Reaction notes

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