Water → 2-Bromo-2-phenylacetamide

HRID 556315Notes

Reaction equation

HRID 556315 reaction equation
[C:1]1([CH2:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11]N1C(=O)CCC1=O.O>ClCCl>[Br:11][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([NH2:10])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 7680BenzeneacetamideHCID 67184N-bromobutanimide

Product 1

HCID 2420282-Bromo-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzeneacetamide (3.0 g, 0.022 mol) was dissolved in dichloromethane (60 mL) and N-bromosuccinimide (4.0 g, 0.022 mol) was added. The reaction was stirred at room temperature under UV light for 24 hr. The mixture was poured into water and the layers were separated. The organic layer was washed with water (2×50 mL) then with brine (1×50 mL). The organic layer was dried (magnesium sulfate) then chromatographed on silica (40% ethyl acetate/hexanes) to give 2-Bromo-2-phenylacetamide, compound h Rf 0.37, 40% ethyl acetate/hexanes; MS m/z 216 (M+H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water (2×50 mL)
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. customthen chromatographed on silica (40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-eccf5d443a924dc2b747e9b9781c3046
Source dataset
uspto-grants-2011_11
Patent number
US08058274B2

Reaction notes

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