Sodium Hydroxide → 3-BROMO-2-CHLOROQUINOLINE

HRID 1492111Notes

Reaction equation

HRID 1492111 reaction equation
O=P(Cl)(Cl)[Cl:3].[Br:6][C:7]1[CH:8]=[N+:9]([O-])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[OH-].[Na+]>>[Br:6][C:7]1[C:8]([Cl:3])=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 8180763-bromoquinoline 1-oxide

Product 1

HCID 112187363-BROMO-2-CHLOROQUINOLINEYield 80.4%

Procedure

To POCl3 (7.5 ml, 80 mmol) was added in portions solid 6 (2.25 g, 10 mmol). The mixture was stirred at room temperature for 30 min and then 60° C. for 10 min. The mixture was then poured into cold 1M NaOH extracted with CH2C2. The combined extracts were dried (K2CO3) and concentrated to a residue which was purified by flash chromatography (EtOAc) to afford 3-Bromo-2-chloroquinoline 7 (1.95 g, 80%). 1H NMR d (ppm): 7.6 dd (CH atom), 7.7 m (2 CH atom), 8.0 d (CH atom), 8.5 s (CH arom)

Workup

  1. wait60° C. for 10 min
  2. extractionextracted with CH2C2
  3. dry with materialThe combined extracts were dried (K2CO3)
  4. concentrationconcentrated to a residue which
  5. customwas purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-f0016692235f46fe996292d88622d558
Source dataset
uspto-grants-1994_12
Patent number
US05372813

Reaction notes

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