6-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide → 6-Bromo-2,2,3-trimethyl-2,3-dihydro-1-benzothiophene-3-ol 1,1-dioxide

HRID 2390296Notes

Reaction equation

HRID 2390296 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6](=[O:13])[C:7]([CH3:12])([CH3:11])[S:8](=[O:10])(=[O:9])[C:4]=2[CH:3]=1.[CH3:16][Mg]Br>CCOCC>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]([CH3:16])([OH:13])[C:7]([CH3:11])([CH3:12])[S:8](=[O:9])(=[O:10])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 565941096-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide2×HCID 178418573HCID 178418573, compound

Product 1

HCID 565941126-Bromo-2,2,3-trimethyl-2,3-dihydro-1-benzothiophene-3-ol 1,1-dioxideYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A cooled (0° C.) solution of 6-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide (Intermediate 241; 750 mg; 2.59 mmol) in anhydrous Et2O (22.5 ml) was treated carefully with a 3 M solution of methylmagnesium bromide in Et2O (2.6 ml; 7.8 mmol). The white solution was stirred at RT for 1.5 before being quenched with a saturated solution of NH4Cl in water. The phases were separated and the aqueous phase was extracted with Et2O. The combined organic phases were washed with water and brine, dried over anhydrous magnesium sulfate and concentrated to dryness to afford the title compound as a white solid (767 mg, 97%).

Workup

  1. custombefore being quenched with a saturated solution of NH4Cl in water
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with Et2O
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2d7b0e3609354945a7a45f2c4c77f6a5
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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