Potassium Carbonate → HCID 19430532, compound

HRID 1077989Notes

Reaction equation

HRID 1077989 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[OH:29])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[O:22][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 804592-Benzyloxyphenol

Product 1

HCID 19430532HCID 19430532, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 4-fluoro-3-nitrobenzotrifluoride (2.1 g) and 2-benzyloxyphenol (2.0 g) in 10mL of DMF was added potassium carbonate (1.4 g). The reaction was heated at 90° C. for 16 hours. The solution was cooled to room temperature and H20 (10mL) was added. The mixture sas wxtraced with CH2Cl (2×10mL), and the combined extracts were dried (MgSO4), filtered, and concentrated to afford an oil. Silica gel chromatography (ethyl acetate/hexanes) afforde 3.6 g of the title compound. 1H NMR (400 MHz, CDCl3) δ8.19 (s, 1H), 7.60 (d, 1H), 7.26 (m, 5H), 7.08 (m, 4H), 6.88 (d, 1H), 5.02 (s, 2H).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. additionH20 (10mL) was added
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford an oil

Sources & evidence

ORD record
ord-6416587b37104050b5b0560cda7bae54
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

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