Tetrahydrofuran → 2,4-Difluoro-5-sulfobenzoic acid

HRID 1992156Notes

Reaction equation

HRID 1992156 reaction equation
[BH4-].[Na+].Cl[S:4]([C:7]1[C:8]([F:17])=[CH:9][C:10]([F:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13])(=[O:6])=[O:5].C1C[O:21]CC1>>[F:16][C:10]1[CH:9]=[C:8]([F:17])[C:7]([S:4]([OH:21])(=[O:6])=[O:5])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 107535965-(Chlorosulfonyl)-2,4-difluorobenzoic acid

Product 1

HCID 587279372,4-Difluoro-5-sulfobenzoic acidYield 100%

Procedure

Sodium borohydride (0.59 g, 15.6 mmol, 8 equiv) was added portionwise to a solution of 5-(chlorosulfonyl)-2,4-difluorobenzoic acid 885-6a (0.5 g, 1.9 mmol, 1 equiv) in 10 mL THF at 0° C. The reaction was stirred at this temperature for 1 h and then concentrated down and the residue acidified to pH 2 with 5N HCl. The precipitate was removed by filtration and the liquid concentrated down to provide 2,4-difluoro-5-sulfobenzoic acid 885-6b as a white solid (433 mg, 100% yield)

Workup

  1. concentrationconcentrated down
  2. customThe precipitate was removed by filtration
  3. concentrationthe liquid concentrated down

Sources & evidence

ORD record
ord-f08651a63b354b6c8b3ed5d43fe6b90f
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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