Phosphorus oxychloride → Methyl 4-(6-chloropyridin-3-yl)benzoate

HRID 2356087Notes

Reaction equation

HRID 2356087 reaction equation
O[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178497536HCID 178497536, compound

Product 1

HCID 22730372Methyl 4-(6-chloropyridin-3-yl)benzoate

Procedure

A solution of Example 252E (1.2 g, 5 mmol) in POCl3 (30 mL) was heated to reflux for 30 minutes. The excess POCl3 was removed under vacuum and the remaining product was purified by flash column chromatography on silica gel with 4:1 ethyl acetate/hexanes to provide the desired product. MS (ESI) m/e 248 (M+H)+.

Workup

  1. temperatureto reflux for 30 minutes
  2. customThe excess POCl3 was removed under vacuum
  3. customthe remaining product was purified by flash column chromatography on silica gel with 4:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9d8c404d0cd641c996079a93cfa82114
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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