Dimethylformamide → 4-Benzyloxy-1-(3-(4-chlorophenoxy)propyloxy)-2,6-dichlorobenzene

HRID 362444Notes

Reaction equation

HRID 362444 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([OH:16])=[C:11]([Cl:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Cl:17])[C:12]([O:16][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[C:13]([Cl:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2235341-(3-Bromopropoxy)-4-chlorobenzeneHCID 120841702,6-Dichloro-4-benzyloxyphenol

Product 1

HCID 542216784-Benzyloxy-1-(3-(4-chlorophenoxy)propyloxy)-2,6-dichlorobenzeneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5.0 g of 4-benzyloxy-2,6-dichlorophenol, 4.7 g of 1-bromo-3-(4-chlorophenoxy)propane and 30 ml of N,N-dimethylformamide was added 2.7 g of potassium carbonate with stirring at room temperature. After stirring at room temperature for 12 hours, the reaction solution was poured into iced water and extracted twice with 200 ml of diethyl ether. The ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography to give 6.5 g of 4-benzyloxy-1-(3-(4-chlorophenoxy)propyloxy)-2,6-dichlorobenzene(yield: 85 %).

Workup

  1. stirringAfter stirring at room temperature for 12 hours
  2. extractionextracted twice with 200 ml of diethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain a crude product

Sources & evidence

ORD record
ord-62d6decaa56a4879b6b15aee9dae13fa
Source dataset
uspto-grants-1999_02
Patent number
US05869506

Reaction notes

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