Water → benzyl N-(2-bromoethyl)carbamate

HRID 715108Notes

Reaction equation

HRID 715108 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].[OH-].[Na+].Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].O>O1CCOCC1>[Br:2][CH2:3][CH2:4][NH:5][C:9](=[O:10])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 278694benzyl N-(2-bromoethyl)carbamateYield 183%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Treat a 0° C. solution of 2-bromoethylamine hydrobromide (50 g, 0.246 mol) in dioxane (500 mL) with aqueous NaOH (1 M, 492 mL, 0.492 mol), add benzyl chloroformate (21.6 g, 0.127 mol) drop-wise, warm to RT and stir overnight. Pour the mixture into H2O, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Petroleum ether) to afford the title compound (60 g, 95%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.37-7.33 (m, 5H), 5.12 (s, 2H), 3.61 (t, J=5.6 Hz, 2H), 3.47 (t, J=5.6 Hz, 2H).

Workup

  1. extractionextract with EtOAc (3×)
  2. washwash the combined organics with brine
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate to dryness
  5. custompurify via silica gel chromatography (EtOAc/Petroleum ether)

Sources & evidence

ORD record
ord-253471fbae534987afc5800fc7e0f280
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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