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

Participants

Role	Name	HCID	Charge
Reactant	tert-Butanol	HCID 6386	—
Reactant	1,1'-Carbonyldiimidazole	HCID 68263	—
Reactant	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Reactant	3-Chloro-4-(methoxycarbonyl)benzoic acid	HCID 14372235	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-Chloro-4-(tert-butoxycarbonyl)benzoic acid methyl ester	HCID 54288988	—

Reaction Conditions

Temperature	40 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06521666B1
Source dataset	uspto-grants-2003_02
ORD ID	ord-507df729fab64d6abe69f8a774209bbf
Source note	uspto-grants-2003_02