HCID 13527237, compound → HCID 19261709, compound

HRID 1888731Notes

Reaction equation

HRID 1888731 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7]=2[CH:16]=1.C(Cl)Cl.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7]=2[CH:16]=1

Participants

4

Reactant 2

HCID 13527237HCID 13527237, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 19261709HCID 19261709, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 5-methoxy-1-benzothiophene-2-carboxylate (1.77 g, 7.49 mmol) in methylene chloride (15 mL) was added dropwise 1 M boron tribromide methylene chloride solution (22.5 mL, 22.5 mmol) at −20° C., and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was poured into ice, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solution was passed through silica gel. The solvent was evaporated under reduced pressure, and the obtained solid was washed with hexane to give the title compound (1.53 g, yield 92%).

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-d137df1dacc94300b28c9b24b312ace5
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

Loading…