Dimethylformamide → HCID 68486376, compound

HRID 1428819Notes

Reaction equation

HRID 1428819 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[CH3:26].CN(C=O)C>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[CH3:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 113352,6-DimethylphenolHCID 11430Potassium CarbonateHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 68486376HCID 68486376, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,6-dimethylphenol (0.87 g, 7.1 mmol), potassium carbonate (0.98 g, 7.1 mmol), 2-fluoro-5-nitrotoluene (1.0 g, 6.4 mmol) and DMF (20 mL) was stirred at 100° C. for 2 h. The reaction mixture was diluted with 100 mL water and extracted with 250 mL EtOAc. The organic layer was washed with brine, dried with sodium sulfate and concentrated to provide the crude titled compound (1.5 g, 92%). This material was used without purification: MS (ESI): mass calcd. for C15H15NO3, 257.3; m/z found, 258.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.16 (dd, J=2.8, 0.7 Hz, 1H), 7.92 (dd, J=9.1, 2.7 Hz, 1H), 7.18-7.07 (m, 3H), 6.33 (d, J=9.0 Hz, 1H), 2.50 (s, 3H), 2.09 (s, 6H).

Workup

  1. extractionextracted with 250 mL EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dd00118303a74fcc9b0299c0868ad8dc
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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