ChemicalBook CAS DataBase List 5-CHLORO-2-(CHLOROMETHYL)-1,3-BENZOXAZOLE

5-CHLORO-2-(CHLOROMETHYL)-1,3-BENZOXAZOLE synthesis

4synthesis methods

Product Name:5-CHLORO-2-(CHLOROMETHYL)-1,3-BENZOXAZOLE
CAS Number:63842-22-8
Molecular formula:C8H5Cl2NO
Molecular Weight:202.04

2-Chloro-N-(5-chloro-2-hydroxyphenyl)acetamide

35588-38-6
9 suppliers
$60.00/100mg

5-CHLORO-2-(CHLOROMETHYL)-1,3-BENZOXAZOLE

63842-22-8
33 suppliers
$67.00/250mg

Yield:63842-22-8 98%

Reaction Conditions:

with toluene-4-sulfonic acid in phenol; for 3 h;Reflux;

Steps:

7.2 Step 2:Preparation of 5-chloro-2-(chloromethyl)benzo[d]oxazole

200 mg of 2-chloro-N-(5-chloro-2-hydroxyphenyl)acetamide (0.91 mmol) obtained in Step 1 was dissolved in 5 ml of phenol, and 78 mg of p-toluenesulfonyl acid (0.45 mmol)) was added, followed by stirring under reflux for 3 hours.
After completion of the reaction, the resultant was extracted with 100 ml of ethyl acetate, washed with 100 ml of an inorganic salt solution, dried over anhydrous sodium sulfate (Na₂SO₄), and concentrated under reduced pressure.
The residue was purified by column chromatography (hexane:ethyl acetate = 10:1, v/v) to give 180 mg of the title compound (0.89 mmol) in 98% yield.
Rf = 0.48 (hexane:ethyl acetate = 5:1, v/v)
¹H NMR (500 MHz, DMSO-d₆) δ 7.93 (d, J = 2.0 Hz, 1H), 7.85 (d, J = 8.6 Hz, 1H), 7.53 (dd, J = 8.6, 2.0 Hz, 1H), 5.09 (s, 2H)

References:

EP3892623,2021,A1 Location in patent:Paragraph 0133