4-Fluorophenol → HCID 9816580, compound

HRID 1290795Notes

Reaction equation

HRID 1290795 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:12]([C:14]1[N:19]2[N:20]=[CH:21][N:22]=[C:18]2[N:17]=[CH:16][CH:15]=1)[CH3:13]>COCCOC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:12]([C:14]2[N:19]3[N:20]=[CH:21][N:22]=[C:18]3[N:17]=[CH:16][CH:15]=2)[CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 189193517-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

Product 1

HCID 9816580HCID 9816580, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

4-Fluorophenol (1.12 g) was added to a stirred suspension of sodium hydride (0.48 g) in dry 1,2-dimethoxyethane (35 ml). The mixture was stirred at room temperature for 30 minutes, then a solution of 7-(1-bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine (2.27 g, prepared in a similar manner to that described in Example 6 below) in dry 1,2-dimethoxyethane (85 ml) was added dropwise. The mixture was stirred at room temperature for 24 hours. The sodium bromide was removed from the mixture by filtration. The solvent was evaporated from the filtrate and the residue dissolved in dichloromethane and washed with 200 ml of a 5% aqueous solution of sodium hydroxide, followed by water. The organic layer was dried over magnesium sulphate. Evaporation of the solvent afforded a crude product which was purified by column chromatography on silica gel using as eluent a mixture of petroleum ether and ethyl acetate (in the ratio 6:4 respectively), followed by recrystallisation from a mixture of ethyl acetate and hexane, to give 7-[1-(4-fluorophenoxy)ethyl]-1,2,4-triazolo[1,5-a]-pyrimidine. Yield 1.03 g, (mp 106°-108° C.).

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at room temperature for 24 hours
  3. customThe sodium bromide was removed from the mixture by filtration
  4. customThe solvent was evaporated from the filtrate
  5. dissolutionthe residue dissolved in dichloromethane
  6. washwashed with 200 ml of a 5% aqueous solution of sodium hydroxide
  7. dry with materialThe organic layer was dried over magnesium sulphate
  8. customEvaporation of the solvent
  9. customafforded a crude product which
  10. customwas purified by column chromatography on silica gel using as eluent
  11. additiona mixture of petroleum ether and ethyl acetate (in the ratio 6:4 respectively),
  12. customfollowed by recrystallisation from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-4d0a11c2e1dd440a9c71d575d2ef126d
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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