Isobutyl chloroformate → HCID 66820246, compound

HRID 473854Notes

Reaction equation

HRID 473854 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl[C:23]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:24]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:23]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:24])[CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 116942652-(4-bromophenyl)-1H-imidazole

Product 1

HCID 66820246HCID 66820246, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-bromophenyl)imidazole (5.3 g, 23.76 mmol) was taken into THF (100 mL) followed by addition of DIPEA (5 mL, 28.5 mmol) and isobutyl chloroformate (3.4 mL, 26.1 mmol) and the resulting solution was stirred for 30 minutes at room temperature. The solution was then concentrated and the residue partitioned with ethyl acetate and water. The organic phase was washed once with 10% aqueous citric acid, brine then dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (2.5:1 hexanes:ethyl acetate) to give isobutyl 2-(4-bromophenyl)-1H-imidazole-1-carboxylate (3.5 g, 46% yield) as an amorphous residue.

Workup

  1. concentrationThe solution was then concentrated
  2. customthe residue partitioned with ethyl acetate and water
  3. washThe organic phase was washed once with 10% aqueous citric acid, brine
  4. dry with materialthen dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (2.5:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-629ee49b37134bb9b8fee4e0cd0a1c10
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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