Phosphorus oxychloride → 1-Chloro-7-(trifluoromethyl)phthalazine

HRID 1896948Notes

Reaction equation

HRID 1896948 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[N:8][N:9]=[C:10]2O)=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:12]=2)[CH:7]=[N:8][N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518898HCID 178518898, compound

Product 1

HCID 585625761-Chloro-7-(trifluoromethyl)phthalazine

Conditions

Temperature
100 °C

Procedure

Into a 50 mL round-bottom flask, was placed 7-(trifluoromethyl)phthalazin-1-ol (prepared as described in the previous step, 1.6 g, 7.48 mmol, 1.00 equiv) and POCl3 (12 mL). The reaction mixture was stirred for 2 h at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was dissolved in 50 mL of dichloromethane, washed with 3×5 mL of H2O, dried (Na2SO4), and concentrated under vacuum. The residue was purified by chromatography over a silica gel column with CH3CN/H2O (10:4). The title compound was obtained as a yellow solid.

Workup

  1. customInto a 50 mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. dissolutionThe residue was dissolved in 50 mL of dichloromethane
  4. washwashed with 3×5 mL of H2O
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography over a silica gel column with CH3CN/H2O (10:4)

Sources & evidence

ORD record
ord-4769d5ee47e04b5fa749ece68c6ec810
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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