Acetone Cyanohydrin → 2-(4-Chloro-2-iodophenyl)acetonitrile

HRID 1868846Notes

Reaction equation

HRID 1868846 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[C:4]([I:10])[CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N:30]([C:38](OC(C)C)=O)=NC(OC(C)C)=O.CC(C)(O)C#N>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:38]#[N:30])=[C:4]([I:10])[CH:3]=1

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 53401425(4-Chloro-2-iodophenyl)methanol

Product 1

HCID 513574012-(4-Chloro-2-iodophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

(4-Chloro-2-iodophenyl)methanol (4.67 g, 17 mmol) and PPh3 (6 mL, 26 mmol) were stirred in Et2O at 0° C. Diisopropyl azodicarboxylate (5 mL, 26 mmol) was added dropwise, and the reaction was stirred for 20 minutes (a white precipitate formed). A solution of acetone cyanohydrin (2 mL, 26 mmol) in diethyl ether (5 mL) was added dropwise to the reaction. The resulting solution was stirred for 5 minutes at 0° C. and then allowed to warm to room temperature over two hours. The reaction was monitored by TLC and LCMS. The mixture was filtered, and the filtrate was concentrated in vacuo. Purification was done using silica flash chromatography with a gradient of 0-15% EtOAc/hexanes. MS m/e=278 (M+H)+.

Workup

  1. customformed)
  2. stirringThe resulting solution was stirred for 5 minutes at 0° C.
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-31973928462d489fb344b9b1c6b55713
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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