Cesium carbonate → HCID 90043425, compound

HRID 1050236Notes

Reaction equation

HRID 1050236 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].CC1C=CC(S(O[CH:21]2[CH2:24][O:23][CH2:22]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:21]2[CH2:24][O:23][CH2:22]2)=[CH:4][C:3]=1[F:9]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27791534-Bromo-3-fluorophenolHCID 13153907Oxetan-3-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 90043425HCID 90043425, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

4-bromo-3-fluorophenol (1.185 g, 6.20 mmol), oxetan-3-yl 4-methyl-benzenesulfonate (1.77 g, 7.75 mmol) and cesium carbonate (5.05 g, 15.51 mmol) were dissolved in DMSO (7.75 mL) and heated to 60° C. overnight. The reaction mixture was diluted with water and EtOAc. The aqueous phase was extracted with EtOAc (×2) and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography on a Biotage™ 50 g column by eluting with 2% to 50% EtOAc:Hexane to give the desired product. 1H NMR δ (ppm) 7.39 (t, 1H), 6.50 (d, 1H), 6.40 (d, 1H), 5.17-5.12 (m, 1H), 4.97 (t, 2H), 4.73 (t, 2H).

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (×2)
  2. washthe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography on a Biotage™ 50 g column
  7. washby eluting with 2% to 50% EtOAc

Sources & evidence

ORD record
ord-379bfa2347dd45259ebe6797281e2506
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

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