ChemicalBook CAS DataBase List 4-BROMO-N-(1,1-DIMETHYLETHYL)BENZAMIDE

4-BROMO-N-(1,1-DIMETHYLETHYL)BENZAMIDE synthesis

12synthesis methods

Product Name:4-BROMO-N-(1,1-DIMETHYLETHYL)BENZAMIDE
CAS Number:42498-38-4
Molecular formula:C11H14BrNO
Molecular Weight:256.14

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Yield:42498-38-4 96%

Reaction Conditions:

Stage #1: 4-bromo-benzaldehydewith sodium azide;trifluorormethanesulfonic acid;acetic acid at 40; for 2 h;Schmidt Reaction;
Stage #2: acetic acid tert-butyl esterwith trifluorormethanesulfonic acid at 40;Ritter Amidation;

Steps:

General procedure for the syntheses of Substituted N-(tert-butyl)benzamides

General procedure: To a magnetically stirred solution of benzaldehyde (1 mmol) and NaN₃ (1.5 mmol) in AcOH (0.2 mL), TfOH (1 mmol) was added and the reaction mixture was heated at 40 °C for 1-2 hrs. On the complete conversion of aldehyde (monitored by TLC) tert-butyl acetate was added alongwith TfOH (1 mmol). The reaction was continued to heating at 40 °C for another 3-5 hrs. After the completion, the reaction was brought to room temperature and ice-cooled aq. sat. NaHCO₃ was added to the reaction mixture. The precipitate formed was filtered and washed with plenty of cold water and dried to obtain the desired benzamide as white solid in 96% yield. (Compounds obtained were pure hence, no further purification or recrystallisation was required).

References:

Singh, Garima;Dada, Ravikrishna;Yaragorla, Srinivasarao [Tetrahedron Letters,2016,vol. 57,# 39,p. 4424 - 4427] Location in patent:supporting information

540-88-5
365 suppliers
$22.00/25mL