Toluene → HCID 22380933, compound

HRID 895717Notes

Reaction equation

HRID 895717 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][C:13]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:14]=1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:6]=[CH:5]2.C1(C)C=CC=CC=1.C(OCC)(=O)C.[CH3:42][N:43](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:42]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][C:13]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:14]=1[C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH:6]=[CH:5]2)#[N:43]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 22380960HCID 22380960, compound

Product 1

HCID 22380933HCID 22380933, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

The compound (t-butyl 2-(6-bromo-2-naphthyloxy)-4-nitrobenzoate) (1.78 g) obtained in a previous production example, zinc cyanide (0.33 g) and tetrakis(triphenylphosphine)palladium (0) (690 mg) were reacted for 12 hours at 100° C. in N,N-dimethylformamide. After cooling to room temperature, toluene and ethyl acetate were added, the organic layer was washed with 2 N ammonia water and saturated saline and dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography (300 g, hexane:ethyl acetate=6:1) to obtain 1.14 g of t-butyl 2-(6-cyano-2-naphthyloxy)-4-nitrobenzoate.

Workup

  1. washthe organic layer was washed with 2 N ammonia water and saturated saline
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by silica gel chromatography (300 g, hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-580e7f49341a46c9b41dce291aa1004f
Source dataset
uspto-grants-2005_07
Patent number
US06916837B2

Reaction notes

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