tert-Butanol → Tert-butyl 4-bromo-3,5-diethoxybenzoate

HRID 1097012Notes

Reaction equation

HRID 1097012 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:14][CH2:15][CH3:16].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:29][C:30](O)([CH3:32])[CH3:31].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[Br:1][C:2]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:5]([C:6]([O:8][C:30]([CH3:32])([CH3:31])[CH3:29])=[O:7])=[CH:4][C:3]=1[O:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 579309874-Bromo-3,5-diethoxybenzoic acid

Product 1

HCID 57930980Tert-butyl 4-bromo-3,5-diethoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 4-Bromo-3,5-diethoxybenzoic acid (2.8 g) in DMF (25 ml) was added CDI (1.8 g) at room temperature and the mixture was stirred at 40° C. for 2 h. To the reaction mixture, t-BuOH (1.85 ml) and DBU (1.752 ml) were added and further stirred at 40° C. for over night. After cooling to room temperature, the mixture was poured into ice-H2O and extracted with EtOAc. The organic layer was washed with H2O, brine and dried over sodium sulphate. After filtration and concentration, the residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound as a colorless solid.

Workup

  1. stirringfurther stirred at 40° C. for over night
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with H2O, brine
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-4cfa29ee4660479a8165d8785cc25a31
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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