Cesium carbonate → HCID 86697223, compound

HRID 237561Notes

Reaction equation

HRID 237561 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+].CC1C=CC(S(O[CH:28]2[CH2:32][CH2:31][C:30]([OH:34])([CH3:33])[CH2:29]2)(=O)=O)=CC=1>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH:28]2[CH2:32][CH2:31][C:30]([CH3:33])([OH:34])[CH2:29]2)=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 86697224HCID 86697224, compound

Product 1

HCID 86697223HCID 86697223, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-bromo-3,5-dimethylphenol (300 mg) and Cs2CO3 (600 mg) in N,N-dimethylformamide (3 mL) is added 3-hydroxy-3-methylcyclopentyl 4-methylbenzenesulfonate (275 mg). The mixture is stirred for 12 hours at 50° C. and then partitioned between water and diethylether. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (petrole ether/ethyl acetate 90:10→30:70). The enantiomers are separated by SFC on chiral phase (column: Daicel IA, 5 μm, 250 mm×10 mm; eluent: scCO2/(methanol+0.2% diethylamine) 85:15, 10 mL/min):

Workup

  1. custompartitioned between water and diethylether
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (petrole ether/ethyl acetate 90:10→30:70)
  5. customThe enantiomers are separated by SFC on chiral phase (column: Daicel IA, 5 μm, 250 mm×10 mm; eluent: scCO2/(methanol+0.2% diethylamine) 85:15, 10 mL/min)

Sources & evidence

ORD record
ord-92247b8849194c108d2a93451b26158f
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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