2,5-Dimethylphenol → HCID 27815831, compound

HRID 1184375Notes

Reaction equation

HRID 1184375 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].Cl[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 72672,5-DimethylphenolHCID 11430Potassium CarbonateHCID 13655Benzonitrile, 4-chloro-3-nitro-

Product 1

HCID 27815831HCID 27815831, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,5-Dimethylphenol (6.99 g, 57.20 mmol) and 4-chloro-3-nitrobenzonitrile (8.00 g, 43.96 mmol) were combined with K2CO3 (30.40 g, 220.00 mmol) in THF (100 mL). The reaction mixture was heated to reflux for 48 hrs and then the solid was filtered through a bed of Celite. After rinsing the residue with copious amounts of EtOAc, the filtrate was washed sequentially with NaHCO3, water, and brine, dried over anhydrous MgSO4, and filtrated. The filtrate was concentrated in vacuo to produce compound 30 as a white powder (10.00 g, 85.0% yield, 99.1% pure). 1H NMR (500 MHz, DMSO-d6): δ 8.65 (d, J=2 Hz, 1H), 8.03 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.28 (d, J=8 Hz, 1H), 7.09 (d, J=8 Hz, 1H), 6.98 (s, 1H), 6.91 (d, J=9 Hz, 1H), 2.28 (s, 3H), 2.07 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 48 hrs
  3. filtrationthe solid was filtered through a bed of Celite
  4. washAfter rinsing the residue with copious amounts of EtOAc
  5. washthe filtrate was washed sequentially with NaHCO3, water, and brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltrated
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2e345c14af1d4963a8ae22720e713ca5
Source dataset
uspto-grants-2014_03
Patent number
US08669247B2

Reaction notes

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