Water → 3-Bromobenzamide

HRID 1675587Notes

Reaction equation

HRID 1675587 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[OH2:10]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]([NH2:6])=[O:10]

Participants

4

Reactant 2

HCID 962Water2×HCID 233813-Bromobenzonitrile

Product 1

HCID 898073-BromobenzamideYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-bromobenzonitrile (0.91 g, 5 mmol) in dioxane (19 mL), NaBO3.4H2O (2.12 g, 13.78 mmol) and H2O (19 mL) were added. The mixture was stirred at 80° C. 16 hours (h), cooled, added of H2O and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and evaporated. Purification of the residue by column chromatography (hexane/EtOAc 2:8) and recrystallization gave the desired product as colorless tablets. Yield 80% (EtOH). Mp: 156-7° C. (lit. 156° C.) (Pearson, D. E. et al., J. Org. Chem., 28: 3147-3149, (1963)). MS (EI): m/z 199 (M+); 183 (100%).

Workup

  1. temperature16 hours (h), cooled
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated
  5. customPurification of the residue
  6. customby column chromatography (hexane/EtOAc 2:8) and recrystallization

Sources & evidence

ORD record
ord-cbfbd1605e87435d9349ebdf4425e360
Source dataset
uspto-grants-2011_08
Patent number
US08003693B2

Reaction notes

Loading…