Hydrochloric Acid → 3-Fluoro-4-(methylsulphonyl)benzyl alcohol

HRID 1754506Notes

Reaction equation

HRID 1754506 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=[O:6].[BH4-].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 212517323-Fluoro-4-methanesulfonylbenzaldehyde

Product 1

HCID 672190853-Fluoro-4-(methylsulphonyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cooled suspension of 3-fluoro-4-methanesulfonyl-benzaldehyde (1.3 g, 6.44 mmol) in ethanol (5 ml) under an inert atmosphere of Argon is added sodium borohydride (0.275 g, 7.27 mmol) portionwise over 2-3 minutes. After stirring for 4 hours, the reaction mixture is poured carefully onto ice-cold water and acidified to pH 1 using 1M HCl. The product is extracted into ethyl acetate (80 ml) and this organic portion is washed with brine, dried over MgSO4 and the solvent is removed in vacuo to give an oil which solidifies on drying to yield the titled compound.

Workup

  1. additionthe reaction mixture is poured carefully onto ice-cold water
  2. extractionThe product is extracted into ethyl acetate (80 ml)
  3. washthis organic portion is washed with brine
  4. dry with materialdried over MgSO4
  5. customthe solvent is removed in vacuo
  6. customto give an oil which
  7. customon drying

Sources & evidence

ORD record
ord-eb02f3ebf4164427b4a69ead2b2fd9ce
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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