3-Bromobenzyl bromide → HCID 19801606, compound

HRID 1646183Notes

Reaction equation

HRID 1646183 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.Cl.[CH3:11][O:12][C:13](=[O:16])[CH2:14][NH2:15]>CO.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][NH:15][CH2:14][C:13]([O:12][CH3:11])=[O:16])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 699793-Bromobenzyl bromideHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 19801606HCID 19801606, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3-bromobenzylbromide (4.3 g, 17.2 mmol) in methanol (25 ml) and triethylamine (5 ml) is treated with glycine methyl ester hydrochloride (4.3 g, 34.4 mmol) and heated to reflux for 18 hours. The solvent is removed in vacuo and the residue chromatographed over silica gel (0-2% methanol in ethyl acetate as eluant) to give 1.62 g of a yellow oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. customThe solvent is removed in vacuo
  4. customthe residue chromatographed over silica gel (0-2% methanol in ethyl acetate as eluant)

Sources & evidence

ORD record
ord-827ba41fcc2a4b23aa0a3eb4ecfb788b
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

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