Allyl iodide → 2-(3,4-Dichlorophenyl)pent-4-enenitrile
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[Li+].[CH3:13][CH:14]([N-]C(C)C)[CH3:15].C(I)C=C>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:15][CH:14]=[CH2:13])[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
3,4-Dichlorophenylacetonitrile (5 g, 26.87 mmol, 1 eq) in THF (50 mL) was cooled to −78° C. under Ar. LDA (2 M in THF, 16.1 mL, 32.2 mmol, 1.2 eq) was added and the reaction was warmed to 0° C. over 1 h. The reaction was re-cooled to −78° C. and allyl iodide (2.67 mL, 26.87 mmol, 1 eq) was added then the reaction was stirred at −78° C. for a further 2 h. The reaction was diluted with EtOAc (150 mL) and washed with aqueous HCl (1 M, 100 mL), saturated aqueous Na2S2O3 (100 mL) and saturated aqueous NaCl (100 mL). The organic extracts were dried over Na2SO4, filtered and concentrated by rotary evaporation to afford 2-(3,4-dichlorophenyl)-pent-4-ene-nitrile (6.3 g, ˜28 mmol) as a yellow oil.
Workup
- temperatureThe reaction was re-cooled to −78° C.
- washwashed with aqueous HCl (1 M, 100 mL), saturated aqueous Na2S2O3 (100 mL) and saturated aqueous NaCl (100 mL)
- dry with materialThe organic extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
Sources & evidence
- ORD record
- ord-81613f03a89249128cda679a082e508d
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07034056B2
Reaction notes
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