Cesium carbonate → 4-(4-Bromo-3,5-dimethylphenoxy)tetrahydro-2H-pyran

HRID 237451Notes

Reaction equation

HRID 237451 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+].CS(O[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)(=O)=O>CN1CCCC1=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 11344352Oxan-4-yl methanesulfonate

Product 1

HCID 866971154-(4-Bromo-3,5-dimethylphenoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (3 g) in N-methyl-pyrrolidone (10 mL) is slowly added Cs2CO3 (9.7 g) and tetrahydro-2H-pyran-4-yl methanesulfonate (5.4 g). The mixture is heated for 3 hours at 140° C. After cooling to room temperature the mixture is partitioned between saturated aqueous Na2CO3 solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (MgSO4). The solvents are evaporated and the residue is purified by HPLC on reversed phase to give the title compound. Yield: 1.2 g; LC (method 4): tR=1.83 min.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customis partitioned between saturated aqueous Na2CO3 solution and ethyl acetate
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried (MgSO4)
  5. customThe solvents are evaporated
  6. customthe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-681e0752718944dfa4ac8743b00107c0
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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