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

HRID 2170927Notes

Reaction equation

HRID 2170927 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+].[O:17]1[CH2:22][CH2:21][CH:20](OS(C)(=O)=O)[CH2:19][CH2:18]1>CN1C(=O)CCC1>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH:20]2[CH2:21][CH2:22][O:17][CH2:18][CH2:19]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

Reaction under argon atmosphere: 3.0 g (15 mmol) of 4-bromo-3,5-dimethylphenol are dissolved in 20.0 ml NMP. 20.0 g (61.4 mmol) of cesium carbonate and 11.0 g (61.0 mmol) of methanesulfonic acid tetrahydropyran-4-yl ester are added. The reaction mixture is stirred at 140° C. for 4 h. The solvent is evaporated. The residue is diluted with EtOAc and washed with water and brine. The organic layer is dried and the solvent is evaporated. The residue is chromatographed on silica gel (CH/EtOAc=99/1→60/40) to give the title compound. Yield: 4.0 g; LC (method 1): tR=1.15 min; Mass spectrum (ESI+): m/z=285 [M+H]+.

Workup

  1. customReaction under argon atmosphere
  2. customThe solvent is evaporated
  3. additionThe residue is diluted with EtOAc
  4. washwashed with water and brine
  5. customThe organic layer is dried
  6. customthe solvent is evaporated
  7. customThe residue is chromatographed on silica gel (CH/EtOAc=99/1→60/40)

Sources & evidence

ORD record
ord-260ad74cf85840018cf2ffc733192fb5
Source dataset
uspto-grants-2015_06
Patent number
US09051289B2

Reaction notes

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