Dimethylformamide → HCID 22996227, compound

HRID 1167296Notes

Reaction equation

HRID 1167296 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH3:13].[CH3:14][N:15](C)C=O>C(OCC)C.C(=O)(O)[O-].[Na+].[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>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]#[N:15])=[C:3]([O:10][CH2:11][CH2:12][CH3:13])[CH:4]=1

Participants

7

Reactant 2

HCID 6228DimethylformamideHCID 229962121-Bromo-4-methoxy-2-propoxy-benzene

Product 1

HCID 22996227HCID 22996227, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 1-bromo-4-methoxy-2-propoxy-benzene (500 mg, 2.04 mmol) in dimethylformamide (10 mL) at room temperature was added zinc cyanide (240 mg, 2.04 mmol). The reaction mixture was degassed by passing argon through for 2 h before tetrakis(triphenylphosphine)palladium (236 mg, 0.204 mmol) was added. The reaction mixture was heated at 90-100° C. under argon for 12 h. The reaction mixture was taken up in diethyl ether (10 mL) and sodium bicarbonate solution (2 mL). The product was extracted with diethyl ether (2×20 mL). The organic layers were washed with water (1×5 mL), brine (1×5 mL), 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 15-20% ethyl acetate in hexanes yielded 4-methoxy-2-propoxy-benzonitrile (290 mg, 74%) as white solids.

Workup

  1. customThe reaction mixture was degassed
  2. customthrough for 2 h
  3. additionwas added
  4. extractionThe product was extracted with diethyl ether (2×20 mL)
  5. washThe organic layers were washed with water (1×5 mL), brine (1×5 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe solid was then filtered off
  8. concentrationthe filtrate was concentrated in vacuo
  9. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  10. washeluting with 15-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-edad628ce2f84917a9920d775e20f723
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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