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

HRID 2168733Notes

Reaction equation

HRID 2168733 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-677ed4b117a442719865b5de947786fe
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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