ChemicalBook CAS DataBase List N-(TERT-BUTOXYCARBONYL)-3-BROMOANILINE

N-(TERT-BUTOXYCARBONYL)-3-BROMOANILINE synthesis

6synthesis methods

Product Name:N-(TERT-BUTOXYCARBONYL)-3-BROMOANILINE
CAS Number:25216-74-4
Molecular formula:C11H14BrNO2
Molecular Weight:272.14

24424-99-5 Synthesis

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Yield: 100%

Reaction Conditions:

in sodium hydroxide

Steps:

14.1 Step 1.
Step 1. N-t-Boc-3-bromoaniline 3-bromoaniline (10 g, 58.1 mmol) and di-tert-butyldicarbonate (19.0 g, 87.1 mmol) were dissolved in 2M aqueous sodium hydroxide and heated at reflux for 1 hour. After cooling to ambient temperature, the reaction mixture was extracted with ethyl acetate. The organic layer was washed (saturated aqueous ammonium chloride, 1*; water, 1*; and brine, 2*), dried (MgSO₄), filtered, concentrated in vacuo, and dried under high vacuum to provide N-t-Boc-3 bromoaniline as a colorless solid (15.8 g, 100%). mp 83° C. ¹ H NMR (300 MHz, CDCl₃) δ 7.66 (1H, br m), 7.08-7.23 (3H, m), 6.46 (1H, br s), 1.52 (9H, s). MS m/e 272/274 (M+H)⁺, 289/291 (M+NH₄)⁺.

References:

Abbott Laboratories US5407959, 1995, A