Water → 4,5-Difluoro-6-phenoxypyrimidine

HRID 2187091Notes

Reaction equation

HRID 2187091 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[F:14][C:15]1[C:20]([F:21])=[C:19](F)[N:18]=[CH:17][N:16]=1.O>O1CCCC1>[O:7]([C:19]1[C:20]([F:21])=[C:15]([F:14])[N:16]=[CH:17][N:18]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 35727644,5,6-TrifluoropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 158696744,5-Difluoro-6-phenoxypyrimidineYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 42.4 g (0.45 mol) of phenol and 50.4 g (0.45 mol) of potassium tert-butoxide in 400 ml of tetrahydrofuran is added dropwise at 0° C. to a solution of 80 g (0.6 mol) of 4,5,6-trifluoropyrimidine in 1 of tetrahydrofuran. When the addition was complete, the reaction mixture was stirred for 30 minutes at 0° C. and then poured into water and extracted using ethyl acetate. The organic phase is dried over sodium sulphate and concentrated in vacuo, and the residue is stirred with low-boiling petroleum ether. 63.8 g (68.1% of theory) of 4-phenoxy-5,6-difluoropyrimidine of melting point 65-66° C. are obtained.

Workup

  1. additionWhen the addition
  2. extractionextracted
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. stirringthe residue is stirred with low-boiling petroleum ether

Sources & evidence

ORD record
ord-8367ec30ecc443dfa94abe7686250feb
Source dataset
uspto-grants-2002_06
Patent number
US06407233B1

Reaction notes

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