Potassium Carbonate → HCID 86624792, compound

HRID 1867260Notes

Reaction equation

HRID 1867260 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Cl)/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.CCOC(C)=O>[C:21]1(/[CH:20]=[CH:19]/[CH2:18][O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[N+:9]([O-:11])=[O:10])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1362364-Fluoro-2-nitrophenolHCID 639658Cinnamyl chloride

Product 1

HCID 86624792HCID 86624792, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

4-Fluoro-2-nitrophenol (13.5 g, 86 mmol) was dissolved in anhydrous DMF (100 mL) under an N2 atmosphere and treated sequentially with K2CO3 (23.7 g, 172 mmol) and trans-cinnamyl chloride (13.4 g, 87.6 mmol) and heated to 60° C. for 12 h. Upon completion, the reaction was diluted with EtOAc (500 mL), and washed with H2O (3×300 mL) and sat. aq. NaCl (500 mL). The organic layer was dried with MgSO4, filtered and concentrated to yield a yellow solid which was easily recrystallized from EtOAc/hexanes to provide pure 4-fluoro-2-nitrophenyl (2E)-3-phenylprop-2-enyl ether (5-1). 1H NMR (300 MHz, CDCl3) δ 7.61 (dd, J=7.5, 2.5 Hz, 1H), 7.41 (app d, J=7.0 Hz, 2H), 7.34 (t, J=7.5 Hz, 2H), 7.27 (m, 2H), 7.12 (dd, J=9.0, 4.0 Hz, 1H), 6.76 (d, J=16.0 Hz, 1H), 6.37 (dt, J=16.0, 5.5 Hz, 1H), 4.83 (dd, J=5.5, 1.0 Hz, 2H).

Workup

  1. washwashed with H2O (3×300 mL) and sat. aq. NaCl (500 mL)
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield a yellow solid which
  6. customwas easily recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-d050323b154f40beb2ac38e72b31df4d
Source dataset
uspto-grants-2009_12
Patent number
US07632833B2

Reaction notes

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