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

Participants

Role	Name	HCID	Charge
Reactant	Trimethyl orthoformate	HCID 9005	—
Reactant	Ytterbium triflate	HCID 2733225	—
Reactant	2-Amino-5-bromo-4-chlorophenol	HCID 58487100	—
Solvent	Ethanol	HCID 702	—
Product	6-Bromo-5-chloro-2-methylbenzoxazole	HCID 58487438	90.3%

Reaction Conditions

Temperature	90 °C

Reaction Steps

A mixture of 2-amino-5-bromo-4-chlorophenol (53) (4.746 g, 21.1 mmol), trifluoromethanesulfonic acid Ytterbium (III) salt (130 mg, 1% mol) and trimethyl orthoformate (4.03 ml, 1.5 eq.) in 15 ml EtOH was heated at 90° C. for 1 h. After cooling down to r.t. Crystalline formed was filtered, washed with MeOH, dried to give 4.694 g 54 as pale brown fine needles (yield: 90.3%)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08754219B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-4bcc88ca57ad416286455a0b1eecb180
Source note	uspto-grants-2014_06