Potassium Carbonate → 4-Chloro-1-nitro-2-(phenyl-2-propenyloxy)benzene

HRID 1197480Notes

Reaction equation

HRID 1197480 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.BrC[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH2:15].[C:22](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH2:22][CH:15]=[CH:14][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11900Phenol, 5-chloro-2-nitro-HCID 234998(3-bromoprop-1-en-2-yl)benzene

Product 1

HCID 544105374-Chloro-1-nitro-2-(phenyl-2-propenyloxy)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-chloro-2-nitrophenol (7 g) in dimethylformamide (40 ml) was stirred at room temperature with 1-bromo-2-phenyl-2-propene (8 ml) and potassium carbonate (5.5 g) for 18 h. The reaction mixture was diluted with water (200 ml) was extracted with ether (100 ml). The ether was washed with water (3×100 ml). The solvent was removed under reduced pressure and the residue was crystallized from hexanes. The yellow solid (8.6 g) was the desired product. m.p. 74.5°-75.5° C.

Workup

  1. extractionwas extracted with ether (100 ml)
  2. washThe ether was washed with water (3×100 ml)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was crystallized from hexanes

Sources & evidence

ORD record
ord-41ee3afac9f448dbbedb89d25e36269c
Source dataset
uspto-grants-1994_01
Patent number
US05276039

Reaction notes

Loading…