HCID 21949748, compound → HCID 86617327, compound

HRID 1918449Notes

Reaction equation

HRID 1918449 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:11]=[CH:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.ClCCl.[Br-].[Br-].[Br-]>C(Cl)(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:11]=[CH:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21949748HCID 21949748, compoundHCID 86617328HCID 86617328, compound

Product 1

HCID 86617327HCID 86617327, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To chloroform (80 ml) solution of phenyl N-(4-methoxyphenyl)-3-(phenoxy)acrylimidate (2.4 g) was added dropwise with borone tribromide dichloromethane solution (1.0M: 14.0 ml) under ice-cooling and stirred for one hour at the same temperature and 2.5 hours at room temperature. Chloroform (200 ml) was added to the reaction solution and it was successively washed with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain phenyl N-(4-hydroxyphenyl)-3-(phenoxy)acrylimidate (0.46 g) as white crystal.

Workup

  1. temperaturecooling
  2. washwas successively washed with water and aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-9c512349cb0c4d6cb39441d379b3553c
Source dataset
uspto-grants-2013_12
Patent number
US08618329B2

Reaction notes

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