Water → HCID 15058610, compound

HRID 711010Notes

Reaction equation

HRID 711010 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][CH2:9][F:10].[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])#[N:12].O>CN(C=O)C>[F:10][CH2:9][CH2:8][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 119072-HydroxybenzonitrileHCID 129822-Fluoroethyl bromide

Product 1

HCID 15058610HCID 15058610, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

K2CO3 (1.74 g, 12.5 mmol) and 1-bromo-2-fluoro ethane (0.78 mL, 10.47 mmol) were added to a solution of 2-cyanophenol 134 (0.5 g, 4.19 mmol) in anhydrous DMF (10 mL), and heated at 70° C. for 45 min. After completion, the reaction mixture was cooled to room temperature and water (10 mL) was added and the mixture extracted with diethyl ether. The combined organic layer was washed with brine, dried (Na2SO4), filtered and evaporated. The residue was purified on flash silica gel column chromatography (hexane:ethyl acetate=2:1) to give the compound 135 (0.586 g, 84%) as a white solid. 1H NMR (CDCl3, 300 MHz) d 7.51-7.58 (m, 2H), 6.98-7.07 (m, 2H), 4.89 (t, J=3.9 Hz, 1H), 4.73 (t, J=4.2 Hz, 1H), 4.40 (t, J=3.9 Hz, 1H), 4.31 (t, J=3.9 Hz, 1H). HRMS calculated for C8H7NOF (M+H)+: 152.0513. found 152.0539.

Workup

  1. temperatureAfter completion, the reaction mixture was cooled to room temperature
  2. extractionthe mixture extracted with diethyl ether
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on flash silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b60bf9d22edf478eb5213b1c934cac52
Source dataset
uspto-grants-2015_11
Patent number
US09181253B2

Reaction notes

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