Hexane → HCID 89815318, compound

HRID 2172326Notes

Reaction equation

HRID 2172326 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.CC(C)([O-])C.[Li+].CCCCCC.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1F.[NH4+].[Cl-]>C1COCC1.O1CCOCC1>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][C:25]=1[N:3]1[C:2]([CH3:1])=[CH:6][N:5]=[CH:4]1

Participants

8

Reactant 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 1424144-Bromo-3-fluorobenzotrifluorideHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 178418800HCID 178418800, compound

Product 1

HCID 89815318HCID 89815318, compoundYield 14.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

A solution of 4-methyl-1H-imidazole (1.352 g, 16.46 mmol) in 20 mL THF was treated with lithium tert-butoxide 1N in hexane (16.46 ml, 16.46 mmol) and was allowed to stir for one hour. The reaction mixture was concentrated and then transferred to a microwave vial charged with 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (2.360 ml, 16.46 mmol) and 10 mL dioxane. The reaction mixture was heated to 180° C. in a microwave reactor for one hour. After cooling to room temperature, the reaction mixture was poured into saturated NH4Cl solution and was extracted with DCM. The organics were concentrated. then purified directly by silica gel column chromatography (0 to 50% EtOAc/heptane) yielding 1-(2-bromo-5-(trifluoromethyl)phenyl)-5-methyl-1H-imidazole (0.710 g, 2.327 mmol).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. temperatureAfter cooling to room temperature
  3. extractionwas extracted with DCM
  4. concentrationThe organics were concentrated
  5. customthen purified directly by silica gel column chromatography (0 to 50% EtOAc/heptane)

Sources & evidence

ORD record
ord-7f2dc17dfc6c44d88e911825509fa931
Source dataset
uspto-grants-2015_06
Patent number
US09051311B2

Reaction notes

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