Dimethylformamide → HCID 22996197, compound

HRID 1167341Notes

Reaction equation

HRID 1167341 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH3:10])[CH:5]=[C:4]([CH2:11][O:12][CH3:13])[CH:3]=1.[CH3:14][N:15](C)C=O>C1(C)C=CC=CC=1.[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>[CH3:13][O:12][CH2:11][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH2:8][O:9][CH3:10])[CH:5]=1)[C:14]#[N:15]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 151342111-bromo-3,5-bis(methoxymethyl)Benzene

Product 1

HCID 22996197HCID 22996197, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-bromo-3,5-bis-methoxymethyl-benzene (522 mg, 2.130 mmol) in dimethylformamide (5 mL) at room temperature was added zinc cyanide (150 mg, 1.278 mmol). The reaction mixture was degassed by passing argon through for I h before tetrakis(triphenylphosphine)palladium (148 mg, 0.128 mmol) was added. The reaction mixture was heated at 80° C. under argon for 12 h. The reaction mixture was taken up in toluene (30 mL) and washed with 10% ammonium hydroxide (2×40 mL), brine and dried over anhydrous magnesium 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 20% ethyl acetate in hexanes yielded 3,5-bis-methoxymethyl-benzonitrile (320 g, 79%).

Workup

  1. customThe reaction mixture was degassed
  2. additionwas added
  3. washwashed with 10% ammonium hydroxide (2×40 mL), brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solid was then filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  8. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-504ce8f7cd514fa1b2e12fdb8c63b2f6
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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