2-Tert-Butylphenol → HCID 23013781, compound

HRID 1821677Notes

Reaction equation

HRID 1821677 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[Cl:18][C:19]1[N:20]=[N:21][C:22]([Cl:27])=[CH:23][C:24]=1[O:25][CH3:26].[Cl-].[NH4+]>CS(C)=O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:19]1[N:20]=[N:21][C:22]([Cl:27])=[CH:23][C:24]=1[O:25][CH3:26])([CH3:4])([CH3:2])[CH3:3].[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:22]1[N:21]=[N:20][C:19]([Cl:18])=[C:24]([O:25][CH3:26])[CH:23]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 69232-Tert-ButylphenolHCID 25517Ammonium ChlorideHCID 64013433,6-dichloro-4-methoxypyridazineHCID 23665647Potassium tert-butoxide

Product 2

HCID 23013781HCID 23013781, compoundYield 23.5%HCID 23014101HCID 23014101, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

5.87 g (39.1 mmol) of 2-tert-butylphenol, dimethylsulfoxide (80 mL) and 4.38 g (39.0 mmol) of potassium t-butoxide were mixed, and the mixture was stirred at room temperature for 20 minutes. To the mixture was added a dimethylsulfoxide solution (60 mL) containing 6.92 g (38.7 mmol) of 3,6-dichloro-4-methoxypyridazine, and the resulting mixture was stirred at room temperature for 40 minutes, and at 80° C. for 45 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layers were combined, washed with water, and then, with brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (available from Merck Co., 9385, hexane:ethyl acetate, gradient) to obtain 2.66 g (9.09 mmol, Yield: 23.5%) of 3-(2-tert-butylphenoxy)-6-chloro-4-methoxypyridazine and 1.82 g (6.22 mmol, Yield: 16.1%) of 6-(2-tert-butylphenoxy)-3-chloro-4-methoxypyridazine.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 40 minutes
  2. waitat 80° C. for 45 minutes
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialwith brine, and dried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. customthe residue was purified by silica gel column chromatography (available from Merck Co., 9385, hexane:ethyl acetate, gradient)

Sources & evidence

ORD record
ord-9fc3f553e7ae4f098746383d6094794e
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

Loading…