Phosphorus oxychloride → 6-Bromo-1-chloro-isoquinoline

HRID 2307788Notes

Reaction equation

HRID 2307788 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](O)=[N:7][CH:6]=[CH:5]2.O=P(Cl)(Cl)[Cl:15]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:15])=[N:7][CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517609HCID 178517609, compound

Product 1

HCID 222502446-Bromo-1-chloro-isoquinolineYield 62%

Procedure

A solution of 6-bromo-1-hydroxylisoquinoline (9.205 g, 41.0 mmol) in POCl3 (100 mL) was heated to 100° C. for 4 h. The reaction was concentrated to dryness. The residue was dissolved in ethyl acetate and the organic layer was washed with 5% NaHCO3, water, brine, dried over MgSO4 and concentrated. The residue was was chromatographed on silica gel eluting with CH2Cl2:hexane (3:7) to give the title compound (6.176 g, 62%). MS (DCI/NH3) m/z 241, 243 (M+1)+.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe organic layer was washed with 5% NaHCO3, water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was was chromatographed on silica gel eluting with CH2Cl2:hexane (3:7)

Sources & evidence

ORD record
ord-a2409b0dd24d472e9cf96ed33e0f2591
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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