Nitrogen → (4-Bromo-2-chlorophenyl)acetonitrile

HRID 906839Notes

Reaction equation

HRID 906839 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([Cl:10])[CH:3]=1.N#N.[Si]([C:17]#[N:18])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CC#N>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:17]#[N:18])=[C:4]([Cl:10])[CH:3]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzene

Product 1

HCID 58762522(4-Bromo-2-chlorophenyl)acetonitrileYield 80.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Bromo-1-bromomethyl-2-chloro-benzene (3.04 g, 10.7 mmoles) was dissolved into anhydrous CH3CN. To this mixture (under N2 at ambient temp) was added TMSCN (2.1 mL, 15.7 mmoles) followed by 1.0M TBAF (15.7 mL, 15.7 mmoles, soln in THF). The resulting mixture was stirred at ambient temperature for 15 min after which time it was evaporated in vacuo to yield crude residue. The crude residue was purified using flash silica chromatography (0-10% EtOAc/Hexane) to yield (4-bromo-2-chloro-phenyl)-acetonitrile (1.98 g, 80%) as an off-white solid. 1H-NMR (CDCl3): δ 7.60 (d, J=2.0 Hz, 1H), 7.47 (dd, J′=8.1 Hz, J″=1.8 Hz, 1H), 7.39 (d, J=8.1 Hz, 1H), 3.79 (s, 2H).

Workup

  1. customwas evaporated in vacuo
  2. customto yield crude residue
  3. customThe crude residue was purified

Sources & evidence

ORD record
ord-1852eac9037c42328e40a5dbf8f960e7
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

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