Phosphorus oxychloride → Methyl 5,6-dichloro-2-(3-fluorophenyl)nicotinate

HRID 717826Notes

Reaction equation

HRID 717826 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].P(Cl)(Cl)([Cl:22])=O>>[Cl:1][C:2]1[C:3]([Cl:22])=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66993068Methyl 5-chloro-2-(3-fluorophenyl)nicotinate 1-oxide

Product 1

HCID 58515941Methyl 5,6-dichloro-2-(3-fluorophenyl)nicotinateYield 75%

Conditions

Temperature
90 °C

Procedure

Methyl 5-chloro-2-(3-fluorophenyl)nicotinate 1-oxide (3.0 g, 11 mmol) was stirred in phosphoryl chloride (30 mL) and heated at 90° C. for 1 hour. Evaporation and purification by flash column chromatography using ethyl acetate in hexanes (0-20%) gave the desired compound (2.4 g, 75%). LCMS calculated for C13H9Cl2FNO2 (M+H)+: m/z=300.0, 302.0. found: 299.8, 301.8. 1H NMR (300 MHz, CDCl3): δ 8.23 (s, 1H), 7.40 (m, 2H), 7.22 (m, 1H), 7.17 (m, 1H), 3.73 (s, 3H).

Workup

  1. customEvaporation and purification by flash column chromatography

Sources & evidence

ORD record
ord-2475302ec5c349218fffdda30033e5d6
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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