Phosphorus oxychloride → 7-Bromo-1-Chloroisoquinoline

HRID 14258

Reaction equation

HRID 14258 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2O)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:15]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[Cl:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517616HCID 178517616, compound

Product 1

HCID 65020247-Bromo-1-ChloroisoquinolineYield 85.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 7-bromoisoquinolin-1-ol (2.5 g, 11.1 mmol) and POCl3 (10.4 mL, 111 mmol) was stirred at 70° C. for 2.5 h. The reaction mixture was cooled to room temperature, poured into ice water, and the solution was stirred overnight. The aqueous mixture was diluted with chloroform, washed with a saturated solution of NaHCO3, saturated NaCl, dried (MgSO4), filtered, and concentrated under reduced pressure to afford 7-bromo-1-chloroisoquinoline (2.3 g): 1H NMR (300 MHz, DMSO-d6) δ 8.39-8.36 (m, 2H), 8.09-8.02 (m, 2H), 7.95 (d, J=6 Hz, 1H).

Workup

  1. washwashed with a saturated solution of NaHCO3, saturated NaCl
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d6d13cf4e33436e8f7d59f215952097
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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