Phosphorus oxychloride → HCID 58085779, compound

HRID 249829Notes

Reaction equation

HRID 249829 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]([O:14][CH3:15])=[O:13])=[C:6]2[C:10]=1[O:9][C:8](=S)[NH:7]2.P(Cl)(Cl)(Cl)(Cl)[Cl:17].P(Cl)(Cl)(Cl)=O>>[Cl:17][C:8]1[O:9][C:10]2[C:6](=[C:5]([C:12]([O:14][CH3:15])=[O:13])[CH:4]=[CH:3][C:2]=2[F:1])[N:7]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 58085787HCID 58085787, compound

Product 1

HCID 58085779HCID 58085779, compoundYield 99%

Conditions

Temperature
95 °C

Procedure

A mixture of methyl 7-fluoro-2-thioxo-2,3-dihydrobenzoxazole-4-carboxylate (1.3 g, 5.72 mmol) and phosphorus pentachloride (1.2 g, 5.72 mmol) in phosphorus oxychloride (2.6 mL, 10.25 mmol) was heated to 95° C. for 3.5 h. After cooling to room temperature, the reaction mixture was concentrated and dried under vacuum to afford methyl 2-chloro-7-fluorobenzoxazole-4-carboxylate (1.3 g, quantitative) as a brown solid. 1H NMR (300 MHz, CDCl3) δ 8.08-8.04 (m, 1H), 7.21 (t, J=9.3 Hz, 1H), 4.02 (s, 3H); MS (ESI+) m/z 229 (M+H).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customdried under vacuum

Sources & evidence

ORD record
ord-511ced09b1984c9a9c5b2b29aa905c02
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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