Water → [1,1';3',1'']Terphenyl-2'-yl-acetonitrile

HRID 1181851Notes

Reaction equation

HRID 1181851 reaction equation
Br[CH2:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C-:21]#[N:22].[Na+].O>CN(C=O)C>[C:9]1([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:3]=2[CH2:2][C:21]#[N:22])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 113591842'-Bromomethyl-[1,1':3',1'']terphenyl

Product 1

HCID 69422715[1,1';3',1'']Terphenyl-2'-yl-acetonitrileYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2′-bromomethyl-[1,1′:3′,1″]terphenyl (Tetrahedron Lett. 42; 5467-5472 (2001)) (1.65 g, 5.1 mmol) and sodium cyanide (0.27 g, 5.6 mmol) in 10 mL of DMF was stirred at room temperature overnight. The reaction mixture was poured into water, extracted with diethyl ether and dried over magnesium sulfate. The solvent was removed and the residue was purified by silica gel chromatography (eluting with 0-4% ethyl acetate in hexane) to give [1,1′;3′,1″]terphenyl-2′-yl-acetonitrile as a white solid (0.78 g, 57%): MS (ESI) m/z 270.1 (M+H); HRMS calcd for C20H15N, 270.1277. Found (ESI+): 270.1274; 1H NMR (DMSO-d6): δ 3.57 (s, 2H), 7.20-7.50 (m, 13H).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed
  4. customthe residue was purified by silica gel chromatography (eluting with 0-4% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a418af9e3ba94fac9509e26bf75b3cb1
Source dataset
uspto-grants-2007_10
Patent number
US07285682B2

Reaction notes

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