Sodium methanesulfinate → HCID 67341497, compound
Reaction equation
[Na+].[CH3:2][S:3]([O-:5])=[O:4].Br[C:7]1[CH:8]=[C:9]([CH2:14][OH:15])[CH:10]=[C:11]([F:13])[CH:12]=1>CS(C)=O.CCOC(C)=O.[Cu]I>[F:13][C:11]1[CH:10]=[C:9]([CH2:14][OH:15])[CH:8]=[C:7]([S:3]([CH3:2])(=[O:5])=[O:4])[CH:12]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
Methanesulphinic acid sodium salt (748 mg, 7.33 mmol) was added to (3-bromo-5-fluorophenyl)methanol (501 mg, 2.44 mmol) and copper(I) iodide (0.248 mL, 7.33 mmol) in DMSO (12 mL) under nitrogen. The resulting mixture was stirred at 90° C. for 3 days. The reaction mixture was diluted with EtOAc (300 mL), then filtered. The filtrate was washed sequentially with water (200 mL) and saturated brine (2×200 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 70 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford [3-fluoro-5-(methylsulfonyl)phenyl]methanol (240 mg, 48.1%) as a white solid.
Workup
- filtrationfiltered
- washThe filtrate was washed sequentially with water (200 mL) and saturated brine (2×200 mL)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- customevaporated
- customto afford crude product
- customThe crude product was purified by flash silica chromatography, elution gradient 70 to 100% EtOAc in isohexane
- customPure fractions were evaporated to dryness
Sources & evidence
- ORD record
- ord-efdbf89e5d3d48bda33a352e1fa21338
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003649B2
Reaction notes
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