Hydrogen Bromide → 3-(Bromomethyl)-1-ethylpyrrolidine

Reaction equation

[CH2:1]([N:3]1[CH2:7][CH2:6][CH:5]([CH2:8]O)[CH2:4]1)[CH3:2].[BrH:10].C(=O)([O-])[O-].[Na+].[Na+]>>[Br:10][CH2:8][CH:5]1[CH2:6][CH2:7][N:3]([CH2:1][CH3:2])[CH2:4]1

Participants

Reactant 3

HCID 260Hydrogen Bromide

HCID 10340Sodium Carbonate

HCID 21702849(1-Ethylpyrrolidin-3-yl)methanol

Product 1

HCID 215104953-(Bromomethyl)-1-ethylpyrrolidine

Procedure

A mixture of 5.0 g. (0.0388 mol.) of N-ethyl-3-hydroxymethylpyrrolidine and 50 ml. of 48% hydrogen bromide was refluxed for 17 hours. The reaction mixture was cooled, made basic by addition of solid sodium carbonate and extracted twice with methylene chloride. The combined extracts were dried (MgSO4) and evaporated to dryness to give 3-bromomethyl-N-ethylpyrrolidine.