Reaction #640539

Reaction equation

2,6-Dimethylaniline

ethyl bromoacetate

N-(2,6-Dimethylphenyl)glycine hydrobromide salt

→

N-(2,6 Dimethylphenyl)glycine

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherA precipitated
2. 2
   Otherformed which
3. 3
   Otherwas collected
4. 4
   Othertriturated with dichloromethane (25 mL)

Procedure

2,6-Dimethylaniline (6.1 g, 50.4 mmol), and ethyl bromoacetate (8.4 g, 50.4 mmol) were refluxed neat for 10 min. The reaction mixture was cooled to room temperature and poured into dichloromethane (75 mL). A precipitated formed which was collected and triturated with dichloromethane (25 mL). N-(2,6-Dimethylphenyl)glycine hydrobromide salt (1.21 g, 4.6 mmol, 9.0%) was collected as a white crystalline solid. 1H NMR (CD3OD) d 2.48 (s, 6H), 4.29 (s, 2H), 7.00-7.10 (m, 3H).

Source