Ethyl bromoacetate → HCID 58790086, compound

HRID 418724Notes

Reaction equation

HRID 418724 reaction equation
[I:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[H-].[Na+].Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>C1COCC1>[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 178506559HCID 178506559, compound

Product 1

HCID 58790086HCID 58790086, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-iodoimidazole (1.93 g, 9.95 mmol) in dry THF (50 mL) at 0° C. was added sodium hydride (60% dispersion, 0.43 g, 10.8 mmol) and the mixture was stirred for 20 min. Ethyl bromoacetate (1.1 mL, 1.7 g, 10 mmol) was added by syringe and the cloudy mixture was stirred for 15 min. It was then partitioned between ethyl acetate and water. The organic phase was collected, washed with brine, dried (anhydrous MgSO4), filtered, and concentrated. Silica gel chromatography (50%->75% ethyl acetate/hexanes) of the residue provided 372 (1.88 g, 67% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.57 (d, J=1.4, 1H); 7.32 (d, J=1.4, 1H); 4.93 (s, 2H); 4.13 (q, J=8.0, 2H); 1.20 (t, J=7.2, 3H). LRMS (M+H): 281.0.

Workup

  1. stirringthe cloudy mixture was stirred for 15 min
  2. customIt was then partitioned between ethyl acetate and water
  3. customThe organic phase was collected
  4. washwashed with brine
  5. dry with materialdried (anhydrous MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-33769fa45de040d2b9addc90f3a03329
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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