Cesium carbonate → tert-Butyl 2-(4-bromo-3,5-dimethylphenoxy)ethylcarbamate

HRID 237528Notes

Reaction equation

HRID 237528 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].Br[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonate3×HCID 819704-Bromo-3,5-dimethylphenolHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate3×

Product 1

HCID 86697191tert-Butyl 2-(4-bromo-3,5-dimethylphenoxy)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (200 mg) in N,N-dimethylformamide (5 mL) is added tert-butyl 2-bromoethylcarbamate (270 mg) and Cs2CO3 (810 mg). The mixture is stirred for 20 hours at room temperature. tert-Butyl 2-bromoethylcarbamate (110 mg) and Cs2CO3 (325 mg) are added and the mixture is stirred for 4 hours. Again tert-butyl 2-bromoethylcarbamate (110 mg) and Cs2CO3 (325 mg) are added and the mixture is stirred for 12 hours. The mixture is partitioned between water and diethylether. The organic phase is washed with brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→80:20) to give the title compound. Yield: 320 mg; LC (method 8): tR=0.66 min; Mass spectrum (ESI+): m/z=344 [M+H]+.

Workup

  1. stirringthe mixture is stirred for 4 hours
  2. stirringthe mixture is stirred for 12 hours
  3. customThe mixture is partitioned between water and diethylether
  4. washThe organic phase is washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is evaporated
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→80:20)

Sources & evidence

ORD record
ord-c710cc577eaf45ca9a879dbc21c435e7
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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