Sodium borohydride → 6-Bromo-2,2-dimethyl-2,3-dihydro-1-benzothiophene-3-ol 1,1-dioxide

HRID 2390294Notes

Reaction equation

HRID 2390294 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.[BH4-].[Na+]>CO.C(Cl)Cl>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[CH:6]([OH:13])[C:7]([CH3:11])([CH3:12])[S:8](=[O:9])(=[O:10])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 565941096-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide2×

Product 1

HCID 565941116-Bromo-2,2-dimethyl-2,3-dihydro-1-benzothiophene-3-ol 1,1-dioxideYield 97.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) solution of 6-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide (Intermediate 241; 652 mg; 2.25 mmol) in MeOH (15 ml) and DCM (7 ml) was treated with NaBH4 (43 mg; 1.13 mmol) portionwise. The resulting solution was stirred at RT for 1.5 h, before being cooled to 0° C. and carefully quenched with water. The mixture was concentrated under reduced pressure, water was added to the residue and the aqueous phase was extracted three times with DCM. The combined organic phases were washed with brine, dried with MgSO4, filtered and concentrated to dryness to give the title compound as a white solid (637 mg, 97%).

Workup

  1. temperaturebefore being cooled to 0° C.
  2. customcarefully quenched with water
  3. concentrationThe mixture was concentrated under reduced pressure, water
  4. additionwas added to the residue
  5. extractionthe aqueous phase was extracted three times with DCM
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-733b391bbf2c4ad7b887ec3645f502cf
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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