Tetrahydrofuran → [4-Bromo-2-(methanesulfonyl)phenyl]methanol

HRID 42365Notes

Reaction equation

HRID 42365 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1.C1COCC1.[BH4-].[Na+]>CCO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 27610764-Bromo-2-(methylsulfonyl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 59251623[4-Bromo-2-(methanesulfonyl)phenyl]methanolYield 71.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-bromo-2-methansulfonyl-benzaldehyde (1.0 g, 3.88 mmol) in EtOH (11 mL)/THF (2.5 mL) was added NaBH4 (1.29 g, 34.2 mmol) in three portions. The reaction was carefully quenched with water and the product was extracted with EtOAc, dried (Na2SO4), and purified by silica gel chromatography to give 735 mg of (4-bromo-2-methansulfonyl-phenyl)-methanol.

Workup

  1. customThe reaction was carefully quenched with water
  2. extractionthe product was extracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3d88b6e748454650a9020d7c708611a7
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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