tert-Butanol → 2-Chloro-4-(tert-butoxycarbonyl)benzoic acid methyl ester

HRID 24722Notes

Reaction equation

HRID 24722 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:27][C:28](O)([CH3:30])[CH3:29].C1CCN2C(=NCCC2)CC1>CN(C=O)C>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:9]=[CH:8][C:4]([C:5]([O:7][C:28]([CH3:30])([CH3:29])[CH3:27])=[O:6])=[CH:3][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 143722353-Chloro-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 542889882-Chloro-4-(tert-butoxycarbonyl)benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

3-Chloro-4-methoxycarbonylbenzoic acid (0.24 g) was dissolved in DMF (2.5 mL) under N2 then CDI (0.36 g) was added and the resulting mixture was stirred at 40° C. for 2 h. t-BuOH (0.54 mL) and DBU (0.33 mL) were added and the resulting mixture was stirred at 40° C. for 2 days. The mixture was evaporated and the residue was taken up with AcOEt, washed with 1N HCl and sat NaHCO3, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel; eluent: toluene) to give 2-chloro-4-(tert-butoxycarbonyl)benzoic acid methyl ester (216 mg).

Workup

  1. additionwere added
  2. customThe mixture was evaporated
  3. washwashed with 1N HCl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; eluent: toluene)

Sources & evidence

ORD record
ord-2953743c3998430db6fe2c3d11f3f545
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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