ChemicalBook CAS DataBase List Acetamide, N-[(2-hydroxyphenyl)methyl]-

Acetamide, N-[(2-hydroxyphenyl)methyl]- synthesis

11synthesis methods

Product Name:Acetamide, N-[(2-hydroxyphenyl)methyl]-
CAS Number:80311-94-0
Molecular formula:C9H11NO2
Molecular Weight:165.19

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Yield:80311-94-0 71.7%

Reaction Conditions:

with boron tribromide in dichloromethane at -10 - 20; for 2 h;Inert atmosphere;

Steps:

Preparation of N-(2-hydroxybenzyl)acetamide

N-(2-methoxybenzyl)acetamide (6.5 g, 0.036 mol) was dissolved in DCM (100 mL), andthe solution was cooled to -lOoC under nitrogen. To this solution was added BBr3 (15 mL, 0.15mol) dropwise. After addition, the ice bath was removed and the reaction mixture was stirred atroom temperature for 2 hours. The reaction mixture was re-cooled to -lOoC and quenched by5 water (20 mL). The mixture was extracted by DCM (3 x 100 mL), and the organic layer waswashed with water (3 x 100 mL), brine (100 mL) and dried to give the title compound (4.3 g,71.7 %) as a solid. It was used directly in the next step without further purification. lH NMR(300 MHz, DMSO): 8 9.56 (brs, lH), 8.27 (brs, lH), 7.09- 7.03 (m, 2H), 6.79- 6.72 (m, 2H),4.16 (d, 2H, J = 6.0 Hz), 1.87 (s, 3H). LC-MS: 166.2 [M+H]+, tR = 1.15 min.

References:

WO2013/110578,2013,A1 Location in patent:Page/Page column 45; 46