Dimethylformamide → 2-(4-Bromophenyl)-2-methylpropanenitrile
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#N)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:14].[Cl-].[NH4+].C[N:18]([CH3:21])C=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:9])([CH3:14])[C:21]#[N:18])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (4-bromophenyl)acetonitrile (3 g) in N,N-dimethylformamide (45 ml) chilled to 0° C. was added sodium hydride (55 wt %, 1.47 g) portionwise. The reaction mixture was stirred at the same temperature for 15 min Iodomethane (2.86 mL) was added to the mixture at 0° C. dropwise. After being stirred at 0° C. for 10 min then at room temperature for 1 h, the reaction mixture was poured into ammonium chloride aqueous solution and extracted with diisopropyl ether (3 times) and washed with saturated sodium bicarbonate aqueous solution then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (0-10% ethyl acetate in hexanes) gave the product (3.29 g, 96%). 1HNMR (CDCl3) 400 MHz δ: 7.52 (d, J=8.6 Hz, 2H), 7.35 (d, J=8.6 Hz, 2H), 1.71 (s, 6H).
Workup
- additionwas added to the mixture at 0° C. dropwise
- waitat room temperature for 1 h
- extractionextracted with diisopropyl ether (3 times)
- washwashed with saturated sodium bicarbonate aqueous solution
- dry with materialThe organics were dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customPurification by column chromatography (0-10% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-f2b708f43c644ce19373755eb1d8c08a
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569331B2
Reaction notes
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