Dimethylformamide → HCID 22721205, compound

HRID 1582486Notes

Reaction equation

HRID 1582486 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][C:3]=1[O:11][CH:12]([CH3:14])[CH3:13].C(=O)(O)[O-].[Na+].[CH3:20][N:21](C=O)C>C(OCC)C.[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([C:20]#[N:21])=[C:3]([O:11][CH:12]([CH3:14])[CH3:13])[CH:4]=1)[CH3:10]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 22721046HCID 22721046, compound

Product 1

HCID 22721205HCID 22721205, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
102.5 °C

Procedure

To a solution of 1-bromo-4-ethoxy-2-isopropoxy-benzene (0.48 g, 1.85 mmol) in DMF (5 mL) was added zinc cyanide (217 mg, 1.85 mmol). The reaction was degassed by passing argon through the mixture for 2 h before tetrakis(triphenylphosphine)-palladium (0) (0.21 g, 0.185 mmol) was added. The reaction mixture was heated at 100-105° C. under argon for 12 h. The reaction mixture was taken up in diethyl ether (50 mL) and saturated sodium bicarbonate solution (5 mL). The product was extracted with diethyl ether (2×30 mL). The organic layers were washed with water (1×10 mL) and brine (1×10 mL), dried (sodium sulfate) and concentrated. Purification of the crude by Biotage flash chromatography eluting with 10-15% ethyl acetate in hexanes gave 4-ethoxy-2-isopropoxy-benzonitrile as a clear oil (0.31 g, 81%).

Workup

  1. customThe reaction was degassed
  2. customfor 2 h
  3. additionwas added
  4. extractionThe product was extracted with diethyl ether (2×30 mL)
  5. washThe organic layers were washed with water (1×10 mL) and brine (1×10 mL)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customPurification of the crude by Biotage flash chromatography
  9. washeluting with 10-15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f340916fc3d946759a0370fba2eb0ac7
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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