Tetrahydrofuran → Methyl 4-[3-(3-bromophenyl)-1-cyanopropyl]benzoate

HRID 1257450Notes

Reaction equation

HRID 1257450 reaction equation
[C:1]([CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)#[N:2].O1CCCC1.C(O[K])(C)(C)C.[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][CH2:33]Br)[CH:27]=1>O.CN(C)C=O>[Br:25][C:26]1[CH:27]=[C:28]([CH2:32][CH2:33][CH:3]([C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)[C:1]#[N:2])[CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 848548Methyl 4-(cyanomethyl)benzoateHCID 143612163-Bromophenethyl bromideHCID 178418922HCID 178418922, compound

Product 1

HCID 66939300Methyl 4-[3-(3-bromophenyl)-1-cyanopropyl]benzoateYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixed solution of methyl 4-(cyanomethyl)benzoate (3.50 g, 20.0 mmol), tetrahydrofuran (25 mL) and N,N-dimethylformamide (10 ml) was added tert-butoxy potassium (2.69 g, 24.0 mmol) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added 1-bromo-3-(2-bromoethyl)benzene (3.37 mL, 22.0 mmol) at the same temperature, and the mixture was stirred under ice-cooling for 4 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (3.94 g, 55%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 4 hr
  3. extractionextracted with ethyl acetate
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-42dd959c09e7445aa431ff3d0d1e2b41
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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