HCID 9899948, compound → 5-chloro-2-fluoro-2-methanesulfonyl-1-methylindan-1-ol

HRID 434113Notes

Reaction equation

HRID 434113 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([F:16])([S:12]([CH3:15])(=[O:14])=[O:13])[CH2:5]2.[CH3:17][Mg]Br>O1CCCC1.C(OCC)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]([CH3:17])([OH:11])[C:6]([F:16])([S:12]([CH3:15])(=[O:13])=[O:14])[CH2:5]2

Participants

6

Reactant 2

HCID 9899948HCID 9899948, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 98353725-chloro-2-fluoro-2-methanesulfonyl-1-methylindan-1-ol

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

At room temperature, 260 mg (1 mmol) of 5-chloro-2-fluoro-2-methanesulfonylindan-1-one are dissolved in 10 ml of dry tetrahydrofuran, and 0.33 ml of a 3M solution of methylmagnesium bromide in diethyl ether is added dropwise with stirring. The reaction mixture is stirred at 50° C. for 3 h. A further 0.33 ml of the methylmagnesium bromide solution is then added, and the mixture is stirred at room temperature for another hour. After the reaction has ended, the reaction mixture is diluted with ethyl acetate and extracted successively with sat. ammonium chloride solution, sat. sodium bisulfite solution, sat. sodium bicarbonate solution and sat. sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure Chromatographic purification on silica gel (n-heptane/ethyl acetate 60/40) gives 5-chloro-2-fluoro-2-methanesulfonyl-1-methylindan-1-ol of melting point 148° C.

Workup

  1. stirringThe reaction mixture is stirred at 50° C. for 3 h
  2. stirringthe mixture is stirred at room temperature for another hour
  3. extractionextracted successively with sat. ammonium chloride solution, sat. sodium bisulfite solution, sat. sodium bicarbonate solution and sat. sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure Chromatographic purification on silica gel (n-heptane/ethyl acetate 60/40)

Sources & evidence

ORD record
ord-3139c387bd7e4d2186b19a73bd0adb6e
Source dataset
uspto-grants-2003_12
Patent number
US06670401B2

Reaction notes

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