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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2272178Generated: October 29, 2026

Trimethyl orthoacetate → 6-Bromo-5-chloro-2-methylbenzoxazole

https://huagongshe.com/reaction/2272178

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrimethyl orthoacetateHCID 15050—
ReactantYtterbium triflateHCID 2733225—
Reactant2-Amino-5-bromo-4-chlorophenolHCID 58487100—
SolventEthanolHCID 702—
Product6-Bromo-5-chloro-2-methylbenzoxazoleHCID 5848743880.2%

Reaction Conditions

Temperature90 °C

Reaction Steps

A mixture of 2-amino-5-bromo-4-chlorophenol (29) (865 mg, 3.89 mmol), trifluoromethanesulfonic acid Ytterbium (III) salt (24 mg, 1% mol) and trimethyl orthoacetate (610 μl, 1.2 eq.) in 3 ml EtOH was heated at 90° C. for 1 h. After cooling down to r.t., off-white needles fell off, which were filtered, washed with MeOH, water and dried to give 791 mg title compound as off-white crystalline solid. Yield: 80.2%; purity>95%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09120751B2
Source datasetuspto-grants-2015_09
ORD IDord-97835da8ded442649dc31ed92db6ce95
Source noteuspto-grants-2015_09