Lithium Bromide → tert-Butyl N-(2-bromoethyl)carbamate

HRID 412712Notes

Reaction equation

HRID 412712 reaction equation
[Br-:1].[Li+].CS(O[CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=O)=O>O1CCCC1>[Br:1][CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

Product 1

HCID 4103526tert-Butyl N-(2-bromoethyl)carbamateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

Lithium bromide (136 g, 1.56 mol.) was dissolved in tetrahydrofuran (600 mL) at 0° C. The mixture was allowed to warm to 23° C. and then tert-butyl 2-methylsulfonyloxyethylcarbamate (37.39 g, 156 mmol) was added dropwise. The mixture was stirred at 23° C. for 18 hours and concentrated in vacuo. The residue was dissolved in hexanes and the organic layer was washed with water and brine, dried (Na2SO4) and concentrated in vacuo to provide tert-butyl 2-bromoethylcarbamate (33.48 g, 96% yield) as a brown oil; MS (PB-PCI) C7H14BrNO2 m/e calc 224.10; found 225 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in hexanes
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8a1e78ea9384a1eb1da1379f786bcb0
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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