Water → 2-bromo-N,N-diethylacetamide

HRID 2115402Notes

Reaction equation

HRID 2115402 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH2:6]([NH:8][CH2:9][CH3:10])[CH3:7].C(N(C(C)C)C(C)C)C.O>C1COCC1.C(OCC)(=O)C>[Br:1][CH2:2][C:3]([N:8]([CH2:9][CH3:10])[CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 61147Bromoacetyl bromideHCID 81531Diisopropylethylamine

Product 1

HCID 2255452-bromo-N,N-diethylacetamideYield 27%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromoacetyl bromide (20.2 g, 100 mmol) in THF (300 mL) was cooled to 0° C. and treated with diethylamine (7.31 g, 100 mmol). After dropwise addition of ethyldiisopropylamine (15.5 g, 120 mmol) the reaction mixture was allowed to reach RT and was stirred for 90 min. Water (250 mL) and ethyl acetate (300 mL) were added, the layers were separated and the aqueous layer was extracted twice with ethyl acetate (100 mL). The solvents were removed in vacuo and the residue was purified by distillation (bp 120-121° C./24 mbar) to give 5.24 g (27%) of the title compound as pale yellow oil.

Workup

  1. customto reach RT
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted twice with ethyl acetate (100 mL)
  4. customThe solvents were removed in vacuo
  5. distillationthe residue was purified by distillation (bp 120-121° C./24 mbar)

Sources & evidence

ORD record
ord-0f80f2ac806140429844b75e0401eca7
Source dataset
uspto-grants-2008_10
Patent number
US07435815B2

Reaction notes

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