Bromoacetyl bromide → N-(2-bromoacetyl)cyclopropanecarboxamide

HRID 1925146Notes

Reaction equation

HRID 1925146 reaction equation
[CH:1]1([C:4]([NH2:6])=[O:5])[CH2:3][CH2:2]1.[Br:7][CH2:8][C:9](Br)=[O:10]>O1CCOCC1>[Br:7][CH2:8][C:9]([NH:6][C:4]([CH:1]1[CH2:3][CH2:2]1)=[O:5])=[O:10]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 80376Cyclopropanecarboxamide

Product 1

HCID 59233013N-(2-bromoacetyl)cyclopropanecarboxamideYield 97.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Cyclopropanecarboxamide (58.7 g, 690 mmol) in 1,4-Dioxane (1600 ml) was added 2-bromoacetyl bromide (59.9 ml, 690 mmol) at room temperature and stirred for 4 h at 60° C. The reaction mixture was concentrated to dryness. The residue was dissolved in EtOAc and carefully washed with satd. NaHCO3, water then with brine solution, dried over Na2SO4 and concentrated to get N-(2-bromoacetyl)cyclopropanecarboxamide (138 g, 670 mmol, 97% yield) as an off white solid. This material was used without purification. ESI-MS:m/z 208.0 (M+2H)+.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionThe residue was dissolved in EtOAc
  3. washcarefully washed with satd
  4. dry with materialNaHCO3, water then with brine solution, dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-30325aeabe6e4fcf8b30181cab4b9529
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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