Реакция #168510

Уравнение реакции

Benzyl chloroformate

bromoethylamine hydrobromide

triethylamine

→

product 14

Выход 89.0%

(2-Bromoethyl)carbamic acid benzyl ester

Выход 89.0%

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Другоеthe cooling bath was removed
3. 3
   ДругоеThe mixture was transferred to a 2 L separatory funnel
4. 4
   Промывкаsequentially washed with water (2×500 mL), 2N HCl (250 mL), and water (500 mL)
5. 5
   Фильтрацияfiltered through a 100 g pad of silica gel
6. 6
   Промывкаwashed with methylene chloride
7. 7
   ДругоеEvaporation of the solvents

Методика

Benzyl chloroformate (26 mL, 0.176 mole) was added in one portion to a stirring mixture of bromoethylamine hydrobromide (44 g, 0.21 mole), triethylamine (64 mL, 0.46 mole), and methylene chloride (1 L) at below −40° C. After the addition, the cooling bath was removed, and the reaction was allowed to stir for 3 h. The mixture was transferred to a 2 L separatory funnel, and sequentially washed with water (2×500 mL), 2N HCl (250 mL), and water (500 mL). The resulting solution was suction filtered through a 100 g pad of silica gel and washed with methylene chloride. Evaporation of the solvents afforded the product 14 (40 g, 89%) as an oil. 1H NMR (300 MHz, CDCl3) δ 3.46 (t, 2H), 3.60 (q, 2H), 5.11 (s, 2H), 5.20 (br s, 1H), 7.35 (m, 5H).

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