Isopropanol → HCID 86709882, compound

HRID 2167208Notes

Reaction equation

HRID 2167208 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].C(N(CC)CC)C.[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](F)=[O:20])=[N:17][CH:18]=1>O>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([O:4][CH:2]([CH3:3])[CH3:1])=[O:20])=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8471TriethylamineHCID 86709883HCID 86709883, compound

Product 1

HCID 86709882HCID 86709882, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Anhydrous 2-propanol (0.361 g, 6 mmol) and anhydrous tri-ethylamine (0.405 g, 4 mmol) were added drop-wise at room temperature to the 5-fluoropicolinoyl fluoride provided above. The mixture was stirred at room temperature overnight, poured into a separatory funnel with water and extracted with ethyl ether. The organic phase was then washed with water and dried over MgSO4. The solvent was removed with a rotary evaporator. The concentrated crude product was purified using column chromatography (silica gel) with ethyl acetate/hexanes mixture (1/10) as eluent to give 0.17 g (23% yield, 96% LC purity) of desired product as an off-white solid. GC/MS results were consistent with the chemical formula of isopropyl 5-fluoropicolinate: 70 eV EIMS (GC) m/z=142 (43%), 124 (100%), 97 (97%), 96 (93%), 43 (59%). 1H NMR (400 MHz, CDCl3) δ 8.60 (d, J=2.8 Hz, 1H), 8.18 (dd, J=8.8, 4.4 Hz, 1H), 7.52 (ddd, J=8.7, 7.9, 2.9 Hz, 1H), 5.34 (hept, J=6.3 Hz, 1H), 1.43 (d, J=6.3 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ 163.63 (s), 162.32 (s), 159.71 (s), 144.84 (d, J=3.8 Hz), 138.46 (d, J=24.8 Hz), 126.78 (d, J=5.4 Hz), 123.31 (d, J=18.5 Hz), 69.71 (s), 21.81 (s). 19F NMR (376 MHz, CDCl3) δ−120.51.

Workup

  1. customprovided above
  2. extractionextracted with ethyl ether
  3. washThe organic phase was then washed with water
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed with a rotary evaporator
  6. concentrationThe concentrated crude product
  7. customwas purified

Sources & evidence

ORD record
ord-d9503e7384b74789b89baeb02161ee47
Source dataset
uspto-grants-2015_06
Patent number
US09045427B2

Reaction notes

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