Water → 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(2-(phenoxy)phenoxy)acetyl-1H-imidazole

HRID 1078050

Reaction equation

HRID 1078050 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:21][C:22]1[CH:42]=[CH:41][C:25]([CH2:26][N:27]2[C:31]([C:32](=[O:35])[CH2:33]Br)=[C:30]([CH2:36][CH3:37])[N:29]=[C:28]2[CH2:38][CH2:39][CH3:40])=[C:24]([F:43])[CH:23]=1.O>CC(C)=O>[Br:21][C:22]1[CH:42]=[CH:41][C:25]([CH2:26][N:27]2[C:31]([C:32](=[O:35])[CH2:33][O:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:30]([CH2:36][CH3:37])[N:29]=[C:28]2[CH2:38][CH2:39][CH3:40])=[C:24]([F:43])[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 754912-Hydroxydiphenyl etherHCID 194304911-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-bromoacetyl-1H-imidazole

Product 1

HCID 194304711-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(2-(phenoxy)phenoxy)acetyl-1H-imidazoleYield 13%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 0.63 g (3.36 mmol) of 2-phenoxyphenol and 0.62 g (4.48 mmol) of K2CO3 in 75 mL acetone at ambient temperature was added 1.00 g (2.24 mmol) of 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-bromoacetyl-1H-imidazole obtained from Part B of Example 11 in 25 mL acetone. After stirring at reflux overnight, the reaction mixture was poured into water and extracted with 3×100 mL ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and the solvents evaporated under reduced pressure. The crude product was purified by flash column chromatography using 10-40% ethyl acetate in hexane, which provided 0.16 g (6.3%) of a clear oil after evaporation of solvents under reduced pressure. 1H NMR (300 MHz, CDCl3): δ 0.95 (t, 3H, J=7.3 Hz); 1.29 (t, 3H, J =7.3 Hz); 1.66 (m, 2H); 2.60 (m, 2H); 2.81 (q, 2H, J=7.3 Hz); 5.00 (s, 2H); 6.38 (t, 1H, J=7.8 Hz); 6.89-7.29 (m, 10H). ##STR106##

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with 3×100 mL ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents evaporated under reduced pressure
  7. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-b418881cfedc4d088b2244dcd50d3642
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Linked notes

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