Water → HCID 86665741, compound

HRID 1191649Notes

Reaction equation

HRID 1191649 reaction equation
[Br:1][C:2]([Br:14])=[CH:3][C:4]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[CH:8]=[CH:7][C:5]=1[NH2:6].Br[CH2:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]([Br:14])=[CH:3][C:4]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[CH:8]=[CH:7][C:5]=1[NH:6][CH2:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 86665740HCID 86665740, compound

Product 1

HCID 86665741HCID 86665741, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-(2,2-dibromovinyl)-4-ethoxyaniline (240 mg), methyl 3-(bromomethyl)benzoate (180 mg) and potassium carbonate (124 mg) in N,N-dimethylformamide (2 mL) was stirred overnight at room temperature. Water was added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (258 mg).

Workup

  1. extractionthis resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-3e082a479fe7410b8f4c4ae892723e6d
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

Loading…