Phosphorus oxychloride → 3-(Benzyloxy)-5-bromo-2-chloropyridine

HRID 2307755

Reaction equation

HRID 2307755 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[N+:11]([O-])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:19]>>[CH2:1]([O:8][C:9]1[C:10]([Cl:19])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 582134893-(benzyloxy)-5-bromopyridine N-oxide

Product 1

HCID 226075323-(Benzyloxy)-5-bromo-2-chloropyridineYield 40%

Procedure

A solution of 3-(benzyloxy)-5-bromopyridine N-oxide (2.0 g, 7.1 mmol) in POCl3 (20 mL) was stirred at 100° C. for 7 hours, cooled to room temperature, concentrated, treated with ethyl acetate (50 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexane to provide the desired product (1.0 g, 40%). MS (DCI/NH3) m/e 299 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additiontreated with ethyl acetate (50 mL)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-541a024c85cd4d3b81f065af2f5575d4
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Linked notes

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