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

HRID 1785814Notes

Reaction equation

HRID 1785814 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-ce4250fbd35d41899f315675d0e98526
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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