Selectfluor → HCID 46218814, compound

HRID 386850Notes

Reaction equation

HRID 386850 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.[O:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][C:29]=2[OH:35])[CH2:24][CH2:23]1>C(#N)C>[F:21][C:32]1[CH:33]=[C:28]([CH:25]2[CH2:24][CH2:23][O:22][CH2:27][CH2:26]2)[C:29]([OH:35])=[CH:30][C:31]=1[OH:34]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 462078331228321-01-4

Product 1

HCID 46218814HCID 46218814, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.65 g of N-fluoro-N′-(chloromethyl)triethylenediamine bis(tetrafluoroborate) are added to a solution of 2 g of 4-(tetrahydropyran-4-yl)benzene-1,3-diol (Example 1) in 20 ml of acetonitrile at 0° C. The reaction mixture is stirred for 16 hours at ambient temperature. The reaction mixture is extracted with ethyl acetate, and the organic phases are washed and then dried over sodium sulphate. The residue is chromatographed on silica gel (9/1 heptane/ethyl acetate). 200 mg of 4-fluoro-6-(tetrahydropyran-4-yl)benzene-1,3-diol are obtained. Yield=10%.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. washthe organic phases are washed
  3. dry with materialdried over sodium sulphate
  4. customThe residue is chromatographed on silica gel (9/1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-b4dcd99fc5c24b99900d5896a52ab525
Source dataset
uspto-grants-2013_02
Patent number
US08372879B2

Reaction notes

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