Phenol → HCID 178516260, compound

HRID 926104Notes

Reaction equation

HRID 926104 reaction equation
F[B-](F)(F)F.[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]#[N:15])=[CH:10][CH:9]=1.[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])(=O)C.[Na+]>C(#N)C>[OH:26][C:20]1[CH:25]=[CH:24][C:23](/[N:15]=[N:14]/[C:11]2[CH:12]=[CH:13][C:8]([S:7]([F:16])([F:17])([F:18])([F:19])[F:6])=[CH:9][CH:10]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 517045Sodium AcetateHCID 1222352754-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

Product 1

HCID 178516260HCID 178516260, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diazonium salt 1 (11.6 mg, 0.0365 mmol), phenol (9.5 mg, 0.10 mmol), and sodium acetate (10.2 mg, 0.124 mmol) were dissolved in 0.21 g of acetonitrile. After 1 month, the solution was filtered through Celite 545. Evaporation of the solvent gave a red oil, which was purified by SiO2 column chromatography (9:1 hexane/ethyl acetate) and following preparative TLC (SiO2, CH2Cl2) afforded 27d as yellow-orange crystals (7.3 mg, 62%); m.p. 110.0-111.0° C. IR (ATR): {tilde over (v)}=3261, 1593, 1505, 1467, 1436, 1402, 1271, 1235, 1142, 1094, 829 cm−1. MS (GC, EI): m/z=324 [M+], 305 [M+-F], 197, 121, 93, 65. 1H NMR (500 MHz, CDCl3): δ=7.92-7.88 (m, 6H), 6.97 (d, J=8.8 Hz, 2H), 5.50 (br. s, 1H) ppm. 13C NMR (125 MHz, CDCl3): δ=159.1 (C), 154.4 (C), 153.7 (C), 147.0 (C), 127.0 (2CH), 125.6 (2CH), 122.5 (2CH), 116.0 (2CH) ppm. 19F NMR (470 MHz, CDCl3): δ=84.1 (quint, J=150 Hz, 1 F), 63.2 (d, J=150 Hz, 4 F) ppm.

Workup

  1. waitAfter 1 month
  2. filtrationthe solution was filtered through Celite 545
  3. customEvaporation of the solvent
  4. customgave a red oil, which
  5. customwas purified by SiO2 column chromatography (9:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a6860ba3c0c344ce814926b7367a7eb2
Source dataset
uspto-grants-2016_03
Patent number
US09284336B1

Reaction notes

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