Phosphorus oxychloride → 6-Bromo-1-chlorophthalazine

HRID 1803494Notes

Reaction equation

HRID 1803494 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[NH:7][N:6]=[CH:5]2.P(Cl)(Cl)([Cl:15])=O.C(N(C(C)C)CC)(C)C>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:15])=[N:7][N:6]=[CH:5]2

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 115359186-Bromophthalazin-1(2h)-one

Product 1

HCID 220304246-Bromo-1-chlorophthalazine

Procedure

A mixture of 6-Bromo-2H-phthalazin-1-one (2.5 g), phosphorous oxychloride (11 mL) and diisopropyl ethyl amine (2 mL) was stirred at RT for 30 min then at 90° C. for 3 h. The reaction was then concentrated under reduced pressure, diluted with ethyl acetate and washed with a saturated solution of NaHCO3, NH4Cl, and brine to afford the desired compound (2.0 g). TLC Rf 0.8 (EA/hexane 2/3).

Workup

  1. waitat 90° C. for 3 h
  2. concentrationThe reaction was then concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed with a saturated solution of NaHCO3, NH4Cl, and brine

Sources & evidence

ORD record
ord-1e6cff1e0cf541f791930c31fc17dafd
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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