Hydrochloric Acid → 5-Chlorobenzo[b]thiophene-3-methanol

HRID 2085768Notes

Reaction equation

HRID 2085768 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:6]=2[S:5][CH:4]=1.C([O-])(=[O:15])C.[K+].Cl>[OH-].[Na+].O1CCOCC1>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]2[S:5][CH:4]=[C:3]([CH2:2][OH:15])[C:7]=2[CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 517044Potassium AcetateHCID 27798573-(Bromomethyl)-5-chloro-1-benzothiophene

Product 1

HCID 27761365-Chlorobenzo[b]thiophene-3-methanol

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-bromomethyl-5-chlorobenzothiophene (2.5 g, 9.56 mmol) and potassium acetate (1.96 g, 20 mmol) in 1M NaOH (40 mL) and dioxane (40 mL) was heated to reflux for 24 hours, adjusted to pH<7 with 1M HCl, and extracted with ethyl acetate (3×). The combined extracts were washed with brine, concentrated, and purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product.

Workup

  1. temperatureto reflux for 24 hours
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined extracts were washed with brine
  4. concentrationconcentrated
  5. custompurified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-92e00df66e1640feab302bb6da8b03a9
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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