Bromocyclopropane → 1-Cyclopropyl-3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-one

HRID 1988161Notes

Reaction equation

HRID 1988161 reaction equation
[CH:1]1(Br)[CH2:3][CH2:2]1.C([Li])(C)(C)C.[F:10][C:11]1[CH:12]=[CH:13][C:14]([O:29][CH3:30])=[C:15]([C:17]([CH3:28])([CH3:27])[CH2:18][C:19](N2CCOCC2)=[O:20])[CH:16]=1>C1COCC1>[CH:1]1([C:19](=[O:20])[CH2:18][C:17]([C:15]2[CH:16]=[C:11]([F:10])[CH:12]=[CH:13][C:14]=2[O:29][CH3:30])([CH3:28])[CH3:27])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 78037BromocyclopropaneHCID 223985283-(5-Fluoro-2-methoxyphenyl)-3-methyl-1-morpholin-4-ylbutan-1-oneHCID 178418306HCID 178418306, compound

Product 1

HCID 223985721-Cyclopropyl-3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-oneYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a solution of cyclopropyl bromide (0.120 g) in THF (0.8 mL) cooled to −70° C., a solution of tert-butyl lithium (1.7 M in pentane, 0.8 mL) was added dropwise over 5 minutes. The mixture was stirred at −70° C. for 30 minutes. A solution of 3-(5-fluoro-2-methoxyphenyl)-3-methyl-1-morpholin-4-ylbutan-1-one (0.29 g) in THF (1 mL) was then added all at once and the mixture was stirred for 30 minutes. The mixture was quenched with EtOH (0.3 mL) and warmed to room temperature. The mixture was diluted with EtOAc, washed with water, dried over sodium sulfate, filtered, and evaporated to give the title compound as an oil (0.23 g).

Workup

  1. stirringwas stirred for 30 minutes
  2. customThe mixture was quenched with EtOH (0.3 mL)
  3. temperaturewarmed to room temperature
  4. additionThe mixture was diluted with EtOAc
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-987f80981fef49e8a9bfb7a4c02a5caa
Source dataset
uspto-grants-2009_06
Patent number
US07553966B2

Reaction notes

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