Water → 4-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenyl 4-bromobutyl ether

HRID 1919756Notes

Reaction equation

HRID 1919756 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:29])([F:28])[C:9]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:25][CH2:26][CH3:27])[CH:19]=1)([O:14][CH2:15][O:16][CH3:17])[C:10]([F:13])([F:12])[F:11].[Br:30][CH2:31][CH2:32][CH2:33][CH2:34]Br.O>CN(C)C=O>[Br:30][CH2:31][CH2:32][CH2:33][CH2:34][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:9]([O:14][CH2:15][O:16][CH3:17])([C:10]([F:12])([F:11])[F:13])[C:8]([F:28])([F:29])[F:7])=[CH:19][C:20]=1[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 592010374-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenol

Product 1

HCID 592350954-[1,1,1,3,3,3-Hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenyl 4-bromobutyl etherYield 71.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (132.4 mg, 0.96 mmol) was added to a mixed solution of 4-[1,1,1,3,3,3-hexafluoro-2-(methoxymethyl)oxypropan-2-yl]-2-propylphenol (221.1 mg, 0.64 mmol) and 1,4-dibromobutane (1.38 g, 6.39 mmol) in N,N-dimethylformamide (20 mL), followed by stirring overnight. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel preparative thin-layer chromatography (hexane:ethyl acetate=10:1) to obtain 219.5 mg of the title compound (yield: 71%) as a colorless oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThen, the organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel preparative thin-layer chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-087fdb8a78c64322bc24964330821712
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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