Dimethylamine → HCID 68871844, compound

HRID 2105836Notes

Reaction equation

HRID 2105836 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH2:12][CH3:13])=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:14][NH:15][CH3:16]>O1CCOCC1>[Br:1][C:2]1[C:3]([O:11][CH2:12][CH3:13])=[CH:4][C:5]([N:15]([CH3:16])[CH3:14])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 68872571HCID 68872571, compound

Product 1

HCID 68871844HCID 68871844, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-4-ethoxy-2-fluoro-benzonitrile (2 g, 8.2 mmol) in 16.5 mL of dioxane was added dimethylamine (16.5 mL, 33 mmol, 2.0 M in tetrahydrofuran). The reaction was stirred at 80° C. overnight. The reaction mixture was concentrated in vacuo. Purification of the crude residue by flash column chromatography (silica gel, eluting with a gradient of ethyl acetate in hexanes) gave 5-bromo-2-dimethylamino-4-ethoxy-benzonitrile (1.95 g, 88%). LC-MS: 269.2 [(M+H)+].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification of the crude residue by flash column chromatography (silica gel
  3. washeluting with a gradient of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7d275ad12e9e4e268f6735576de6c766
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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