1,3-Dibromopropane → HCID 19955518, compound

HRID 1779412Notes

Reaction equation

HRID 1779412 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-ab5641358c8941a08429ea06cba98cc3
Source dataset
uspto-grants-1997_05
Patent number
US05627189

Reaction notes

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