4-Fluorobenzenesulfonyl chloride → Sodium 4-fluorobenzene sulfinate

HRID 2120303Notes

Reaction equation

HRID 2120303 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 4311764Sodium borohydride

Product 1

HCID 421250Sodium 4-fluorobenzene sulfinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-fluorobenzenesulfonyl chloride (2 g, 10.28 mmol) in 50 mL of THF (distilled from Na-benzophenone) is cooled to 0° C. and sodium borohydride (1.9 g, 51.4 mmol) is added portionwise. The reaction is stirred at 0° C. for 2 h, then warmed to RT, and after 2 h, quenched with water (5 mL). The solvent is evaporated and the aqueous residue is acidified by addition of aqueous 6N HCl. The product is taken up in EtOAc, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 4-fluorobenzenesulfinic acid: NMR (DMSO-d6) 7.12 (app t, 2H, J=8.3), 7.5 (dd, 2H, J=8.3, 6); ESI-MS 159 [M−1]−.

Workup

  1. temperaturewarmed to RT
  2. waitafter 2 h
  3. customquenched with water (5 mL)
  4. customThe solvent is evaporated
  5. additionthe aqueous residue is acidified by addition of aqueous 6N HCl
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f0e2ddb06cd34f089b639da575ed870c
Source dataset
uspto-grants-2004_02
Patent number
US06689896B2

Reaction notes

Loading…