Phosphorus oxychloride → 4-(3-Bromo-4-cyclohexyloxy-phenyl)-3-butyl-6-chloro-pyridazine

HRID 1972011Notes

Reaction equation

HRID 1972011 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:16]=[C:17](O)[N:18]=[N:19][C:20]=2[CH2:21][CH2:22][CH2:23][CH3:24])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.O=P(Cl)(Cl)[Cl:28]>>[Br:1][C:2]1[CH:3]=[C:4]([C:15]2[CH:16]=[C:17]([Cl:28])[N:18]=[N:19][C:20]=2[CH2:21][CH2:22][CH2:23][CH3:24])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178441952HCID 178441952, compound

Product 1

HCID 866578204-(3-Bromo-4-cyclohexyloxy-phenyl)-3-butyl-6-chloro-pyridazine

Conditions

Temperature
70 °C

Procedure

A suspension of 5-(3-bromo-4-cyclohexyloxy-phenyl)-6-butyl-pyridazin-3-ol (4.18 mmol, 1.7 g) in POCl3 (20 mL) was kept stirring at 70° C. for 2 h. The reaction mixture was concentrated, to the residue water was added, extracted with ethyl acetate washed with sat NaHCO3 solution, water, brine, dried and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography using a mixture of hexanes in ethyl acetate (9:1) to provide 4-(3-bromo-4-cyclohexyloxy-phenyl)-3-butyl-6-chloro-pyridazine (1.5 g).

Workup

  1. concentrationThe reaction mixture was concentrated, to the residue water
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. washwashed with sat NaHCO3 solution, water, brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant residue was purified by silica gel flash chromatography
  8. additiona mixture of hexanes in ethyl acetate (9:1)

Sources & evidence

ORD record
ord-a7a3973119364c6bad6102c0f4627809
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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