Resorcinol → 4-Fluoro-1,3-dihydroxybenzene

HRID 1370968Notes

Reaction equation

HRID 1370968 reaction equation
F[B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+]([F:21])(CC1)CC2.[C:22]1([CH:29]=[CH:28][CH:27]=[C:25]([OH:26])[CH:24]=1)[OH:23]>C(#N)C.C(OCC)C>[F:21][C:27]1[CH:28]=[CH:29][C:22]([OH:23])=[CH:24][C:25]=1[OH:26]

Participants

5

Reactant 2

HCID 5054ResorcinolHCID 2724933Selectfluor2×

Product 1

HCID 105586404-Fluoro-1,3-dihydroxybenzene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

[1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)] (SELECTFLUOR) (1.61 g., 4.54 mmoles) in anhydrous acetonitrile (50 mL) was treated with resorcinol (0.500 g., 4.54 mmoles) and heated at 100° C. overnight. The reaction was diluted with diethyl ether, washed with H2O (2×), saturated NaHCO3 (2×), brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. MS (DCI) m/z 129 (M+H)+.

Workup

  1. washwashed with H2O (2×), saturated NaHCO3 (2×), brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-eae2048e5f8e457aaa8c9512db1660d6
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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