Isopropanol → HCID 86709880, compound

HRID 2167206Notes

Reaction equation

HRID 2167206 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].C(N(CC)CC)C.[F:12][C:13]1[C:14]([C:22](F)=[O:23])=[N:15][C:16]([F:21])=[C:17]([F:20])[C:18]=1[F:19]>O>[F:12][C:13]1[C:14]([C:22]([O:4][CH:2]([CH3:3])[CH3:1])=[O:23])=[N:15][C:16]([F:21])=[C:17]([F:20])[C:18]=1[F:19]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8471TriethylamineHCID 86709881HCID 86709881, compound

Product 1

HCID 86709880HCID 86709880, compoundYield 48%

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 3,4,5,6-tetrafluoropicolinoyl 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 0.454 g (48% yield, 96% GC purity, 93% LC purity) of desired product as a pale yellow liquid. GC/MS results were consistent with the chemical formula of isopropyl 3,4,5,6-tetrafluoropicolinate: 70 eV EIMS (GC) m/z=196 (31%), 178 (100%), 150 (45%), 100 (26%), 43 (34%). 1H NMR (400 MHz, CDCl3) δ 5.32 (hept, J=6.3 Hz, 1H), 1.42 (d, J=6.3 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ 159.81 to 159.74 (m), 149.22 to 148.78 (m), 148.04 to 147.86 (m), 146.49 to 146.10 (m), 145.65 to 145.47 (m), 138.53 (dd, J=34.3, 11.2 Hz), 135.79 (dd, J=34.4, 11.2 Hz), 129.02 to 128.74 (m), 70.97 (s), 21.60 (s). 19F NMR (376 MHz, CDCl3) δ−80.31 to −80.49 (m), −136.04 to −136.18 (m), −137.10 to −137.25 (m), −149.81 to −149.95 (m).

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-5d8d671a104c4af6807430cdaca8e476
Source dataset
uspto-grants-2015_06
Patent number
US09045427B2

Reaction notes

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