Selectfluor → HCID 59326605, compound

HRID 238614Notes

Reaction equation

HRID 238614 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[CH:6]=1.[F:18][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>C(#N)C.O>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[C:6]=1[F:18]

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 20335012(6-Fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326605HCID 59326605, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (100 mg, 0.277 mmol) in acetonitrile (3 mL) was added 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (255 mg, 0.72 mmol) at 0° C. The resulting mixture was stirred at room temperature overnight, and diluted with water, then extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with brine (20 mL×3), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether) to give (1,6-difluoro-4-hydroxy-naphthalen-2-yl)acetic acid methyl ester (60 mg, 86%) as a yellow solid. MS cald. for C13H10F2O3 252, obsd. (ESI+) [(M+H)+] 253.

Workup

  1. extractionextracted with ethyl acetate (20 mL×3)
  2. washThe combined organic layers were washed with brine (20 mL×3)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-c6c3637291f947e7af348f2556c65bd1
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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