Tetrahydrofuran → [4-Bromo-2-(methanesulfonyl)phenyl]methanol
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction was carefully quenched with water
- extractionthe product was extracted with EtOAc
- dry with materialdried (Na2SO4)
- 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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