Hydrochloric Acid → (4-Chloro-phenyl)-prop-2-ynyloxy-acetonitrile

HRID 1092905

Reaction equation

HRID 1092905 reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH2:7]([O:10][CH:11](OCC#C)[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:8]#[CH:9].Cl>ClCCl.[Bi](Br)(Br)Br>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH:11]([O:10][CH2:7][C:8]#[CH:9])[C:5]#[N:6])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 82115Trimethylsilyl cyanideHCID 576886141-(Bis-prop-2-ynyloxy-methyl)-4-chloro-benzene

Product 1

HCID 57688608(4-Chloro-phenyl)-prop-2-ynyloxy-acetonitrileYield 63%

Reagents, catalysts & solvents 2

HCID 82232bismuth(III) bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of nitrogen, trimethylsilyl cyanide (3.1 g) is added to bismuth (III)bromide (0.22 g) and 1-(bis-prop-2-ynyloxy-methyl)-4-chloro-benzene (6.7 g) in dichloromethane (50 ml) at room temperature. The reaction mixture is stirred for 48 hours at room temperature and then poured into 0.5 M hydrochloric acid (50 ml). The organic phase is separated, dried (magnesium sulfate) and evaporated. Crude (4-chloro-phenyl)-prop-2-ynyloxy-acetonitrile (3.7 g) is obtained as oil.

Workup

  1. customThe organic phase is separated
  2. dry with materialdried (magnesium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-67223f3a283240e8b58aa12805df4b8c
Source dataset
uspto-grants-2012_03
Patent number
US08129560B2

Linked notes

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