1-Iodo-4-nitrobenzene → p-(1-Trifluoromethylheptyloxy)nitrobenzene

HRID 372931

Reaction equation

HRID 372931 reaction equation
[H-].[Na+].[F:3][C:4]([F:14])([F:13])[CH:5]([OH:12])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[H][H].[Na].I[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>O.CN(C=O)C>[F:3][C:4]([F:13])([F:14])[CH:5]([O:12][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

8

Reactant 5

HCID 124951-Iodo-4-nitrobenzeneHCID 24758Sodium hydrideHCID 978042-Octanol, 1,1,1-trifluoro-2×HCID 5360545SodiumHCID 178418361HCID 178418361, compound

Product 1

HCID 15123947p-(1-Trifluoromethylheptyloxy)nitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Into 200 ml of dry DMF containing 2.0 g of sodium hydride (purity 60%), were added dropwise 9.2 g of S-form oa 1-trifluoromethyl-heptanol, at room temperature with such a speed not causing too rapid generation of hydrogen, to prepare sodium salt (alkoxide) of S-form oa 1-trifluoromethyl-heptanol. After the addition was over, stirring was continued further an hour at room temperature, followed by adding thereto 12.4 g of p-iodo-nitro-benzene and then refluxing for 2 hours. After cooling, the product was introduced into iced water, and extracted with hexane. The hexane phase was washed subsequently with water, 1N-hydrochloric acid aqueous solution and then water, followed by purifying with silica gell column to obtain 7.7 g of oily oa p-(1-trifluoromethylheptyloxy)- nitrobenzene.

Workup

  1. customat room temperature
  2. additionAfter the addition
  3. waitwas continued further an hour at room temperature
  4. additionby adding
  5. temperatureAfter cooling
  6. extractionextracted with hexane
  7. washThe hexane phase was washed subsequently with water, 1N-hydrochloric acid aqueous solution
  8. customby purifying with silica gell column

Sources & evidence

ORD record
ord-cf72626921c74d82b46ed2443b5116fd
Source dataset
uspto-grants-1992_11
Patent number
US05160662

Linked notes

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