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

HRID 38481Notes

Reaction equation

HRID 38481 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 (1.75 ml) were added and further stirred at 40° C. overnight. 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 sulfate. After filtration and concentration, the residue was purified by silica gel column chromatography (hexane/EtOAc) to give the intended compound as a colorless solid.

Workup

  1. stirringfurther stirred at 40° C. overnight
  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 sulfate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-f00b6c13bf36458d98b8eb4b5f0cb606
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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