Dimethyl Sulfoxide → HCID 86707827, compound

HRID 1747701Notes

Reaction equation

HRID 1747701 reaction equation
Br[CH:2]([C:4]1[O:5][C:6]2[C:11]([C:12](=[O:21])[C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:3].CS(C)=[O:24]>C(O)CCC>[F:20][C:16]1[CH:15]=[C:14]([C:13]2[C:12](=[O:21])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[O:5][C:4]=2[CH:2]([OH:24])[CH3:3])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 60209038HCID 60209038, compound

Product 1

HCID 86707827HCID 86707827, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-(1-bromoethyl)-3-(3-fluorophenyl)-4H-chromen-4-one (30 g, 86.51 mmol) in DMSO (300 ml), n-butanol (15 ml) was added and heated to 120° C. for 3 h. The reaction mixture was cooled to RT, quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as a off-white solid (16 g, 64%) which was used as such in next step.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-efc277532ad94a6b97bcb5bbb6aa02fd
Source dataset
uspto-grants-2015_10
Patent number
US09150579B2

Reaction notes

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