Methyl iodide → Methyl 2-(3-cyano-4-fluorophenyl)propanoate

HRID 2173230Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[CH3:15][Si]([N-][Si](C)(C)C)(C)C.[Na+].CI>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]([CH3:15])[C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of compound methyl (3-cyano-4-fluorophenyl)acetate (200 mg, 1.03 mmol) in 15 mL of anhydrous THF was cooled to −78° C. NaHMDS (1.11 mmol) was added to the reaction dropwise at −78° C. After the addition, the mixture was stirred at −78° C. for 1 h and then CH3I (160 mg, 1.33 mmol) was added to the reaction dropwise at −78° C. The reaction was warmed to room temperature slowly and stirred at ambient temperature over night. The reaction was quenched with NH4Cl solution, extracted with EtOAc. The orgianic layer was washed with saturated chloride, dried over anhydrous sodium sulfate and concentrated. The residue was purified via preparative TLC to afford methyl 2-(3-cyano-4-fluorophenyl)propanoate.

Workup

additionAfter the addition
temperatureThe reaction was warmed to room temperature slowly
stirringstirred at ambient temperature over night
customThe reaction was quenched with NH4Cl solution
extractionextracted with EtOAc
washThe orgianic layer was washed with saturated chloride
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was purified via preparative TLC

Sources & evidence

ORD record: ord-27aadfc8b9b94f59a221c819c8e2ca17
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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