Ethyl Acetate → HCID 21182284, compound

HRID 1386605Notes

Reaction equation

HRID 1386605 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.[F-:23].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O>[F:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 21182510HCID 21182510, compound

Product 1

HCID 21182284HCID 21182284, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-[4-(7-Bromoheptyloxy)phenyl]bromobenzene (0.25 g) in a solution of tetra n-butylammonium fluoride (tetrahydrofuran solution, 1M, 2.9 ml) was heated to 50° C. for 2 hours. After cooling to ambient temperature, the solution was taken up into a mixture of ethyl acetate (20 ml) and water (20 ml). The separated organic layer was washed with water, brine, and dried over magnesium sulfate. Evaporation gave a residue which was chromatographed on silica gel (30 ml) eluting with a mixture of n-hexane and ethyl acetate (100:0-97:3, V/V). The fractions which contained the objective compound were collected and evaporated a residue which was triturated with n-hexane to give 4-[4-(7-Fluoroheptyloxy)phenyl]bromobenzene (104 mg).

Workup

  1. washThe separated organic layer was washed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation
  4. customgave a residue which
  5. customwas chromatographed on silica gel (30 ml)
  6. washeluting with a mixture of n-hexane and ethyl acetate (100:0-97:3, V/V)
  7. customwere collected
  8. customevaporated a residue which
  9. customwas triturated with n-hexane

Sources & evidence

ORD record
ord-cd7f7e6a63fb4d0a8e4c04d1e35666b0
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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