Cyanuric chloride → 2,4-Dichloro-6-(4-fluorophenoxy)-1,3,5-triazine

HRID 1840102Notes

Reaction equation

HRID 1840102 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[N:11]1[C:18]([Cl:19])=[N:17][C:15](Cl)=[N:14][C:12]=1[Cl:13].[NH4+].[Cl-]>O1CCCC1>[Cl:13][C:12]1[N:11]=[C:18]([Cl:19])[N:17]=[C:15]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:14]=1

Participants

6

Reactant 4

HCID 7954Cyanuric chlorideHCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 27827962,4-Dichloro-6-(4-fluorophenoxy)-1,3,5-triazineYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

EX-632B) To a solution of 4-fluorophenol 1.00 g (8.92 mmol) in 30 mL of tetrahydrofuran at 0° C. was added a 60% dispersion of sodium hydride in mineral oil (0.36 g, 8.92 mmol). After 30 min, cyanuric chloride (1.64 g, 8.92 mmol) was added as a heterogeneous mixture in tetrahydrofuran at 0° C. The reaction mixture was allowed to slowly warm to room temperature. After 14 h, the mixture was cooled to 0° C., and a saturated aq. NH4Cl solution was added. The aqueous solution was extracted with diethyl ether (3×50 mL). The combined ether extracts were washed with brine, dried (MgSO4), and concentrated in vacuo to afford 1.34 g (58%) of the desired 2,4-dichloro-6-(4 fluorophenoxy)-1,3,5-triazine product as an off white solid which was taken on to the next step without purification. MS m/z=260 [M+H]+.

Workup

  1. waitAfter 14 h
  2. temperaturethe mixture was cooled to 0° C.
  3. extractionThe aqueous solution was extracted with diethyl ether (3×50 mL)
  4. washThe combined ether extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-854aead6d21a40d0b947910e019d1f3f
Source dataset
uspto-grants-2004_01
Patent number
US06677353B2

Reaction notes

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