Diethyl Ether → HCID 59251315, compound

HRID 1046636Notes

Reaction equation

HRID 1046636 reaction equation
[CH3:1][Mg+].[Br-].CC[O:6][CH2:7][CH3:8].C(OC([C:14]1[N:15]=[C:16]([C:27]2[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][C:28]=2[Cl:34])[N:17]([C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])[CH:18]=1)=O)C>C1COCC1>[Br:33][C:30]1[CH:31]=[CH:32][C:27]([C:16]2[N:17]([C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[CH:18]=[C:14]([C:7]([OH:6])([CH3:8])[CH3:1])[N:15]=2)=[C:28]([Cl:34])[CH:29]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 59251577HCID 59251577, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 59251315HCID 59251315, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 3.0 M solution of MeMgBr in Et2O (7.0 mL, 21.0 mmol) at 0° C. added slowly a solution of 2-(4-bromo-2-chlorophenyl)-1-(2,6-dichlorophenyl)-1H-imidazole-4-carboxylic acid ethyl ester (2.80 g, 5.90 mmol) in THF (30 mL, anhyd). After addition was completed the flask was removed from the ice-water bath and allowed to warm to ambient temperature. At 50 min the reaction mixture was quenched by addition of satd NH4Cl, extracted with EtOAc, dried (Na2SO4), concentrated and purified by chromatography (silica, EtOAc/Hex, 15:85 to 55:45) to give the title compound (2.1 g, 77%) as a white solid. 1H-NMR (DCM-d2): δ 7.58 (d, 1H), 7.37-7.41 (m, 2H), 7.26-7.32 (m, 2H), 7.11 (d, 1H), 6.93 (s, 1H), 2.73 (br s, 1H), 1.61 (s, 6H).

Workup

  1. additionAfter addition
  2. customwas removed from the ice-water bath
  3. customAt 50 min the reaction mixture was quenched by addition of satd NH4Cl
  4. extractionextracted with EtOAc
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by chromatography (silica, EtOAc/Hex, 15:85 to 55:45)

Sources & evidence

ORD record
ord-16d2ad0cdab74839b7ac9772d83c2d77
Source dataset
uspto-grants-2013_10
Patent number
US08569352B2

Reaction notes

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