3,5-Dimethylphenol → HCID 34039741, compound

HRID 1966041Notes

Reaction equation

HRID 1966041 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]1[CH:21]=[C:22]([OH:27])[CH:23]=[C:24]([CH3:26])[CH:25]=1>C1COCC1>[CH3:19][C:20]1[CH:21]=[C:22]([CH:23]=[C:24]([CH3:26])[CH:25]=1)[O:27][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 79483,5-DimethylphenolHCID 11430Potassium CarbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-

Product 1

HCID 34039741HCID 34039741, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-nitrobenzonitrile (12.00 g, 65.75 mmol) in THF was added potassium carbonate (45.58 g, 328.70 mmol) and 3,5-dimethylphenol (9.658 g, 78.88 mmol). The reaction mixture was refluxed for 17 hrs, whereupon the starting material was consumed (TLC, 25% EtOAc in hexanes). The reaction mixture was then cooled to room temperature, and potassium carbonate was filtered and washed with copious amounts of EtOAc. The filtrate was washed sequentially with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give the crude product as a yellow solid. The solid was triturated with hexanes and filtered to afford compound 21 as a whitish-yellow powder. (15.022 g, 85.2% yield, 100% HPLC purity). 1H NMR (500 MHz, DMSO-d6): δ 8.65 (d, J=2 Hz, 1H), 8.06 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.12 (d, J=9 Hz, 1H), 6.97 (s, 1H), 6.84 (s, 2H), 2.29 (s, 6H).

Workup

  1. temperatureThe reaction mixture was refluxed for 17 hrs, whereupon the starting material
  2. customwas consumed (TLC, 25% EtOAc in hexanes)
  3. filtrationpotassium carbonate was filtered
  4. washwashed with copious amounts of EtOAc
  5. washThe filtrate was washed sequentially with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude product as a yellow solid
  10. customThe solid was triturated with hexanes
  11. filtrationfiltered

Sources & evidence

ORD record
ord-3f1bc857ce0e448da1bc490e06373949
Source dataset
uspto-grants-2013_04
Patent number
US08420639B2

Reaction notes

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