Phosphoric Acid → 2-Bromo-N,N-dibutylacetamide
Reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH2:6]([NH:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH3:9].OP(O)(O)=O>C1(C)C=CC=CC=1>[CH2:6]([N:10]([CH2:11][CH2:12][CH2:13][CH3:14])[C:3](=[O:4])[CH2:2][Br:1])[CH2:7][CH2:8][CH3:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of bromoacetyl bromide (72.3 mL, 830 mmol) in toluene (500 mL) cooled to 0° C. was added a solution of dibutylamine (280.0 mL, 1.66 mol) in toluene (220 mL) via an addition funnel maintaining the reaction temperature below 10° C. Upon completion of the addition, the reaction mixture was stirred at 0° C. for 15 minutes. A solution of 2.5% aqueous H3PO4 (500 mL) was slowly introduced, and the reaction mixture was allowed to warm to room temperature with vigorous stirring. The solution is 2.5% phosphoric acid by weight. The layers were separated and the organic phase washed with water (500 mL) and concentrated to provide the bromoacetamide as a solution in toluene.
Workup
- temperaturemaintaining the reaction temperature below 10° C
- additionUpon completion of the addition
- temperatureto warm to room temperature with vigorous stirring
- customThe layers were separated
- washthe organic phase washed with water (500 mL)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-149f677178004f38b577b127d4094f20
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07365093B2
Reaction notes
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