1,3-Dibromopropane → HCID 19955518, compound

HRID 440984Notes

Reaction equation

HRID 440984 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[Br:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:12][CH2:13][CH2:14][CH2:15][O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:10])([F:11])[F:1]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 679582-Trifluoromethylphenol

Product 1

HCID 19955518HCID 19955518, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under a nitrogen atmosphere, a stirred mixture of 4.0 grams (0.025 mole) of 2-trifluoromethylphenol, 17.8 mL (0.178 mole)of 1,3-dibromopropane, and 9.0 grams (0.065 mole) of potassium carbonate in 120 mL of acetone was heated at reflux for about 18 hours. After this time, the reaction mixture was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished using petroleum ether. The product containing fractions were combined and concentrated under reduced pressure, yielding 5.9 grams of 2-trifluoromethylphenyl 3-bromopropyl ether. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about 18 hours
  3. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure to a residual oil
  4. washElution
  5. additionThe product containing fractions
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90521b5d9f0d484f88ba584e414e3b4e
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

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