1,3-Dibromopropane → 1-(3-Bromopropoxy)-4-(trifluoromethoxy)benzene

HRID 363085Notes

Reaction equation

HRID 363085 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[K+].[K+].[F:12][C:13]([F:23])([F:22])[O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1>CN(C)C=O>[Br:1][CH2:2][CH2:3][CH2:4][O:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:13]([F:12])([F:22])[F:23])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 136722751-(3-Bromopropoxy)-4-(trifluoromethoxy)benzeneYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 20.4 g of 1,3-dibromopropane, 7.1 g of potassium carbonate and 100 ml of N,N-dimethylformamide was added dropwise a solution of 9 g of 4-trifluoromethoxyphenol dissolved in 30 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was filtered, and the solvent was removed from the filtrate by distillation under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 9.1 g of 1-(3-bromopropyloxy)4-trifluoromethoxybenzene (60% yield).

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent was removed from the filtrate by distillation under reduced pressure

Sources & evidence

ORD record
ord-6518c9106a434ce08dcee0bb0fcd8727
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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