Benzyl Bromide → Ethyl 2-(benzyloxyamino)benzoate

HRID 1054212Notes

Reaction equation

HRID 1054212 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:15][NH:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C.O>[CH2:1]([O:15][NH:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 13571167Ethyl 2-(hydroxyamino)benzoate

Product 1

HCID 90257947Ethyl 2-(benzyloxyamino)benzoateYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirring suspension of benzyl bromide (1.038 g, 6.07 mmol) and cesium carbonate (2.70 g, 8.28 mmol) in DMF (4 mL) was added ethyl 2-(hydroxyamino)benzoate (1.0 g, 5.52 mmol) dissolved in 2 mL DMF at RT and stirred for 1 h. Reaction mixture was diluted with water and extracted with EtOAC. The organic layer was separated and distilled out to get crude product which was column purified using 0-3% EtOAC in hexane to get the titled compound in 72% yield.

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAC
  3. customThe organic layer was separated
  4. distillationdistilled out
  5. customto get crude product which
  6. custompurified

Sources & evidence

ORD record
ord-a1e4d6eb2d374331964e9bd1917a3855
Source dataset
uspto-grants-2016_07
Patent number
US09394300B2

Reaction notes

Loading…