Acetone Cyanohydrin → 3-(4-Bromophenyl)propionitrile

HRID 1385171Notes

Reaction equation

HRID 1385171 reaction equation
CCO[C:4](/[N:6]=N/C(OCC)=O)=O.[Br:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19]O)=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)(O)C#N>C(OCC)C>[Br:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][C:4]#[N:6])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 11776TriphenylphosphineHCID 728512-(4-Bromophenyl)ethanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 27356113-(4-Bromophenyl)propionitrileYield 97.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Diethylazodicarboxylate (5.2 g) is added dropwise to a solution of 4-bromo-phenethylalcohol (2.01 g) and triphenylphosphine (7.9 g) in diethyl ether (16 mL) at 0° C. The reaction mixture is stirred for 10 minutes and a solution of acetone cyanohydrin (2.6 g) in diethyl ether (10 mL) is added. The clear orange solution is stirred for 5 minutes at 0° C. and then at 25° C. for 12 hours. The reaction mixture is then filtered, and washed with diethyl ether. The filtrate is concentrated under reduced pressure and chromatographed over silica gel (10% ethyl acetate-hexanes is used as the eluant) to provide the desired product as a pale yellow oil (2.04 g).

Workup

  1. stirringThe clear orange solution is stirred for 5 minutes at 0° C.
  2. waitat 25° C. for 12 hours
  3. filtrationThe reaction mixture is then filtered
  4. washwashed with diethyl ether
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customchromatographed over silica gel (10% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-c76435c117644991b7d4c36bf13171ab
Source dataset
uspto-grants-2001_07
Patent number
US06262082B1

Reaction notes

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