Dimethylformamide → 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(1,1,1,3,3,3-hexafluoro-2-propyloxy)butyloxy)benzene

HRID 369671Notes

Reaction equation

HRID 369671 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:5]=[C:6]([Cl:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.[F:21][C:22]([F:30])([F:29])[CH:23]([OH:28])[C:24]([F:27])([F:26])[F:25].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:5]=[C:6]([Cl:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:28][CH:23]([C:24]([F:27])([F:26])[F:25])[C:22]([F:30])([F:29])[F:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 222571451-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-4-bromobutane

Product 1

HCID 544919273,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(1,1,1,3,3,3-hexafluoro-2-propyloxy)butyloxy)benzeneYield 15.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 0.42 g of 3,5-dichloro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.25 g of 1,1,1,3,3,3-hexafluoro-2-propanol, 0.17 g of potassium carbonate and 10 ml of N,N-dimethylformamide. After stirring at room temperature for 48 hours, the reaction mixture was poured into water and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then concentrated. The residue was subjected to silica gel chromatography, which afforded 0.077 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(1,1,1,3,3,3-hexafluoro-2-propyloxy)butyloxy)benzene (yield, 15%), nD24.0 1.4805.

Workup

  1. extractionextracted twice with diethyl ether
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-71061694b60c45d8974df9e2f6401b3c
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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