m-Chloroperbenzoic acid → HCID 118537054, compound

HRID 923381Notes

Reaction equation

HRID 923381 reaction equation
[F:1][C:2]1[S:6][C:5]2[CH2:7][S:8][CH2:9][C:4]=2[C:3]=1[F:10].C1C=C(Cl)C=C(C(OO)=O)C=1>C(Cl)Cl>[F:1][C:2]1[S:6][C:5]2=[CH:7][S:8][CH:9]=[C:4]2[C:3]=1[F:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 118537058HCID 118537058, compound

Product 1

HCID 118537054HCID 118537054, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An oven-dried 250 ml flask equipped with a magnetic stir bar was charged with 560 mg of 2,3-difluoro-4,6-dihydrothieno[3,4-b]thiophene (3.15 mmol) and 50 ml methylene chloride. The solution was cooled to 0° C. m-CPBA (0.71 g, 77%, 3.15 mmol) was added to one portion and the reaction mixture was allowed to warm up to room temperature overnight. The solvent was removed by a roto-vap and the residue was redissolved in 15 ml acetic anhydride and heated for 2 hours. The acetic anhydride was then removed by roto-vap and the product was purified by column chromatography to produce 199.5 mg of product. (GC-MS found m/q: 176 (Calculated for C6H2F2S2 176.21)

Workup

  1. customAn oven-dried 250 ml flask equipped with a magnetic stir bar
  2. additionwas added to one portion
  3. customThe solvent was removed by a roto-vap
  4. dissolutionthe residue was redissolved in 15 ml acetic anhydride
  5. temperatureheated for 2 hours
  6. customThe acetic anhydride was then removed by roto-vap
  7. customthe product was purified by column chromatography

Sources & evidence

ORD record
ord-a29b7fe96f624353ad8339306bd4e7a2
Source dataset
uspto-grants-2016_03
Patent number
US09278980B2

Reaction notes

Loading…