Cesium carbonate → HCID 90043208, compound

HRID 1050235Notes

Reaction equation

HRID 1050235 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][CH2:23][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][CH2:23][CH2:22]2)=[CH:4][C:3]=1[F:9]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27791534-Bromo-3-fluorophenolHCID 12621595Cyclobutyl 4-methylbenzene-1-sulfonate

Product 1

HCID 90043208HCID 90043208, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

4-bromo-3-fluorophenol (315 mg, 1.648 mmol), cyclobutyl 4-methyl-benzenesulfonate (373 mg, 1.648 mmol), and cesium carbonate (1074 mg, 3.30 mmol) were dissolved in DMSO (1648 μl) 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. 1H NMR δ (ppm) 7.4 (t, 1H), 6.10 (dd, 1H), 6.53 (dd, 1H), 4.60 (quintet, 1H), 2.49-2.43 (m, 2H), 2.21-2.13 (m, 2H), 1.93 (m, 1H), 1.73 (sextet, 1H).

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-824c5e69958e48f094a1b76f7b75cc15
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

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