Water → 3-Chloro-6-fluoro-2-(trifluoromethyl)quinoxaline

HRID 403420Notes

Reaction equation

HRID 403420 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([C:13]([F:16])([F:15])[F:14])[C:8](O)=[N:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:19].O.C(#N)C.O>C(#N)C>[Cl:19][C:8]1[C:7]([C:13]([F:16])([F:15])[F:14])=[N:6][C:5]2[C:10]([N:9]=1)=[CH:11][C:2]([F:1])=[CH:3][CH:4]=2

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 18373917Acetonitrile--water (1/1)HCID 178517315HCID 178517315, compound

Product 1

HCID 866643423-Chloro-6-fluoro-2-(trifluoromethyl)quinoxalineYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
100 °C

Procedure

7-Fluoro-3-(trifluoromethyl)quinoxalin-2-ol (24.1 g) and POCl3 (158.1 g) were combined and warmed to 100° C. for 12 h. The reaction mixture was cooled to room temperature and diluted with acetonitrile (104 mL). To a separate vessel was charged water (320 g) and acetonitrile (124 g), then cooled to 10° C. The reaction mixture was added to the acetonitrile/water mixture over 1 hour. The slurry was cooled to 10° C. for 30 min, then it was filtered and the cake was washed with 2:1 (v/v) water:acetonitrile (3×65 mL). The solid was dried under vacuum at 50° C. for 14 h (24.7 g, 95% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperaturecooled to 10° C
  3. temperatureThe slurry was cooled to 10° C. for 30 min
  4. filtrationit was filtered
  5. washthe cake was washed with 2:1 (v/v) water
  6. customThe solid was dried under vacuum at 50° C. for 14 h (24.7 g, 95% yield)

Sources & evidence

ORD record
ord-032dee8543fa4d639331f25958ea7004
Source dataset
uspto-grants-2014_06
Patent number
US08748374B2

Reaction notes

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