Dimethylformamide → HCID 22996251, compound

HRID 1167326Notes

Reaction equation

HRID 1167326 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13][N:14](C)C=O>C(OCC)C.[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>[CH3:12][O:11][C:3]1[CH:4]=[CH:5][C:6]([CH2:8][O:9][CH3:10])=[CH:7][C:2]=1[C:13]#[N:14]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 139450582-Bromo-1-methoxy-4-(methoxymethyl)benzene

Product 1

HCID 22996251HCID 22996251, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromo-1-methoxy-4-methoxymethyl-benzene (460 mg, 1.991 mmol) in dimethylformamide (5 mL) at room temperature was added zinc cyanide (140.3 mg, 1.195 mmol). The reaction mixture was degassed by passing argon through for 30 min before tetrakis(triphenylphosphine)palladium (138 mg, 0.119 mmol) was added. The reaction mixture was heated at 80° C. for 12 h and stirred at room temperature for 2 d. It was diluted with diethyl ether (50 mL) and washed with sodium bicarbonate solution, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 30% ethyl acetate in hexanes yielded 2-methoxy-5-methoxymethyl-benzonitrile (268 mg, 76%) as a clear oil.

Workup

  1. customThe reaction mixture was degassed
  2. customthrough for 30 min
  3. additionwas added
  4. washwashed with sodium bicarbonate solution, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solid was then filtered off
  7. concentrationthe filtrate was concentrated in vacuo
  8. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  9. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b644c6eee3164fc78f2e78e95a106975
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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