Cesium carbonate → HCID 86697127, compound

HRID 237464Notes

Reaction equation

HRID 237464 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[CH3:7][C:8]1([CH3:15])[CH2:13][O:12]S(=O)[O:10][CH2:9]1.[Br:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20](O)=[CH:19][C:18]=1[CH3:25]>CN(C)C=O>[Br:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([O:10][CH2:9][C:8]([CH3:15])([CH3:7])[CH2:13][OH:12])=[CH:19][C:18]=1[CH3:25]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 108772941003-85-6

Product 1

HCID 86697127HCID 86697127, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave vial Cs2CO3 (5.4 g) is added to a solution of 5,5-dimethyl-[1,3,2]dioxathiane 2-oxide (500 mg) and 4-bromo-3,5-dimethylphenol (670 mg) in N,N-dimethylformamide (5 mL). The vial is sealed and the mixture is heated to 120° C. for 12 hours. The mixture is partitioned between ethyl acetate and water. The organic phase is washed three times with 2 M aqueous NaOH and with brine. After drying (MgSO4) and concentration the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50) to give the title compound. Yield: 372 mg; LC (method 7): tR=1.17 min; Mass spectrum (ESI+): m/z=287 [M+H]+.

Workup

  1. customThe vial is sealed
  2. customThe mixture is partitioned between ethyl acetate and water
  3. washThe organic phase is washed three times with 2 M aqueous NaOH
  4. customAfter drying
  5. concentration(MgSO4) and concentration the residue
  6. customis chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50)

Sources & evidence

ORD record
ord-bb650956094b456a88a5752c85b1f66f
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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