Ethyl Acetate → HCID 15540373, compound

HRID 381276Notes

Reaction equation

HRID 381276 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10](Cl)[N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[F:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:23]=1[C:29]([F:32])([F:31])[F:30].C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:28][C:25]3[CH:26]=[CH:27][C:22]([F:21])=[C:23]([C:29]([F:32])([F:30])[F:31])[CH:24]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 6018544-Fluoro-3-(trifluoromethyl)phenolHCID 6103722-Chloro-4-(4-fluoro-phenyl)-pyrimidine

Product 1

HCID 15540373HCID 15540373, compoundYield 192.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 0.60 g (2.87 mmol) of 2B in 15 ml of dimethylformamide was added 0.46 g of K2CO3 (3.3 mmol) and 0.60 g (3.3 mmol) of 4-fluoro-3-trifluoromethyl-phenol and the resulting mixture heated at 50° C. for 15 hr and 75° C. for 24 hrs. The cooled reaction mixture was poured into a separatory funnel containing 100 mL of ethyl acetate and washed with 2×50 mL water, 3×15 mL 2.5% NaOH solution, 1×30 mL brine, dried and evaporated in vacuuo to yield 1.95 g of a mobile yellow liquid. This material was filtered through a pad of silica and re-crystallized from heptane/ethyl acetate to give 0.49 g white crystalline solid (m.p. 69-74° C.; 48%).

Workup

  1. customThe cooled reaction mixture
  2. additionwas poured into a separatory funnel
  3. washwashed with 2×50 mL water, 3×15 mL 2.5% NaOH solution, 1×30 mL brine
  4. customdried
  5. customevaporated in vacuuo

Sources & evidence

ORD record
ord-af2e4eb754204140bf2ee4121a5ef565
Source dataset
uspto-grants-2001_10
Patent number
US06306866B1

Reaction notes

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