Triethylamine → 2-[1-(4-Bromophenyl)cyclopropyl]acetonitrile
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:11]O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:13]([N:15](CC)CC)C.CS(Cl)(=O)=O.[C-]#N.[Na+]>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:11][C:13]#[N:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
[1-(4-Bromo-phenyl)-cyclopropyl]-methanol (6.00 g, 26.4 mmol) and triethylamine (4.4 mL, 31.5 mmol) were dissolved in CH2Cl2 and cooled to −78° C. Methanesulfonyl chloride (29.2 mmol) was added and the reaction was stirred at 0° C. for 1 hr. The mixture was submitted to aqueous workup and the reaction volume was reduced to 50 mL. Sodium cyanide (3.9 g, 79.6 mmol) and DMF (50 mL) were added and the remaining CH2Cl2 was removed under vacuum. The reaction was then heated to 70° C. for 3 hours, cooled, and submitted to standard aqueous workup to provide the title compound which was used in the next step without further purification.
Workup
- customthe remaining CH2Cl2 was removed under vacuum
- temperatureThe reaction was then heated to 70° C. for 3 hours
- temperaturecooled
Sources & evidence
- ORD record
- ord-9e17f403d4cf4bbf9c31e2da5f244a98
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09272990B2
Reaction notes
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