Triacetoxyperiodinane → 2-Bromo-4-(2-oxoethyl)benzonitrile

HRID 1466027Notes

Reaction equation

HRID 1466027 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[C:8]([CH2:10][CH:11]=[O:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 675145552-Bromo-4-(2-hydroxyethyl)benzonitrile

Product 1

HCID 772307012-Bromo-4-(2-oxoethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-Bromo-4-(2-hydroxyethyl)benzonitrile (220 mg, 1.0 mmol) in DCM (15 mL) was added Dess-Martin reagent (1.2 g, 2.8 mmol) and the mixture was stirred at RT for 4 hours. The mixture was washed with water, dried over Na2SO4, and concentrated in vacuo to give the title product. 1H NMR (400 MHz, CDCl3) δ 9.77 (t, J=1.6 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.55 (d, J=1.6 Hz, 1H), 7.25 (dd, J=7.8, 1.6 Hz, 1H), 3.78 (d, J=1.6 Hz, 2H).

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac5b1efe14c142a1b88d9c20c74d41f6
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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