Cesium carbonate → 3-(4-Bromo-3,5-dimethylphenoxy)-2,2-dimethylpropanenitrile

HRID 237526Notes

Reaction equation

HRID 237526 reaction equation
CC1C=CC(S(O[CH2:12][C:13]([C:16]#[N:17])([CH3:15])[CH3:14])(=O)=O)=CC=1.[Br:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([OH:26])=[CH:21][C:20]=1[CH3:27].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O.C(OCC)C>[Br:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([O:26][CH2:12][C:13]([CH3:15])([CH3:14])[C:16]#[N:17])=[CH:21][C:20]=1[CH3:27]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 252194682-Cyano-2-methylpropyl 4-methylbenzenesulfonate

Product 1

HCID 866971893-(4-Bromo-3,5-dimethylphenoxy)-2,2-dimethylpropanenitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-cyano-2-methylpropyl 4-methylbenzenesulfonate (760 mg) and 4-bromo-3,5-dimethylphenol (500 mg) in N,N-dimethylformamide (8 mL) is added Cs2CO3 (2.0 g). The mixture is stirred for 12 hours at 80° C., diluted with diethylether and washed with water and brine. After drying (MgSO4) the solvent is evaporated and the residue is chromatographed on silica gel (petrole ether/ethyl acetate 90:10→60:40) to give the title compound. Yield: 572 mg; Mass spectrum (ESI+): m/z=282 [M+H]+.

Workup

  1. washwashed with water and brine
  2. dry with materialAfter drying (MgSO4) the solvent
  3. customis evaporated
  4. customthe residue is chromatographed on silica gel (petrole ether/ethyl acetate 90:10→60:40)

Sources & evidence

ORD record
ord-c36fb84f344a4ccfaf149427677352b5
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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