Dimethyl Sulfoxide → HCID 86707826, compound

HRID 1747700Notes

Reaction equation

HRID 1747700 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][C:9]([F:22])=[CH:8][CH:7]=2)[CH3:3].CS(C)=[O:25]>C(O)CCC>[F:22][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[O:5][C:4]([CH:2]([OH:25])[CH3:3])=[C:13]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[C:12]2=[O:21]

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 53234606HCID 53234606, compound

Product 1

HCID 86707826HCID 86707826, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-(1-bromoethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one (15.0 g, 40.84 mmol) in DMSO (150 ml), n-butanol (7.5 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 an off-white solid (7.90 g, 64%). 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.85 (dd, J=8.1, 3 Hz, 1H), 7.54 (dd, J=9.2, 4.2 Hz, 1H), 7.47-7.37 (m, 2H), 7.15-6.98 (m, 3H), 4.74 (quintet, J=6.8 Hz, 1H), 2.23 (d, J=7.4 Hz, 1H), 1.54 (d, J=6.6 Hz, 3H).

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-62135914b36e469e9d1412e4a08e533b
Source dataset
uspto-grants-2015_10
Patent number
US09150579B2

Reaction notes

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