Triacetoxyperiodinane → 3-Fluoro-4-formylbenzonitrile

HRID 2253337Notes

Reaction equation

HRID 2253337 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][OH:11])[C:5]#[N:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=[O:11])[C:5]#[N:6]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 114805433-Fluoro-4-hydroxymethylbenzonitrile

Product 1

HCID 27831503-Fluoro-4-formylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 53B (340 mg, 2.25 mmol) in dichloromethane (10 mL) at room temperature was treated with Dess-Martin periodinane (1.9 g, 4.5 mmol), stirred for 5 minutes, and concentrated. The concentrate was dissolved in ethyl acetate, washed with saturated sodium bicarbonate, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10:1 hexanes/ethyl acetate to provide the desired product. 1H NMR (500 MHz, CDCl3) δ 10.42 (s, 1H), 8.01 (dd, 1H), 7.62-7.58 (m, 1H), 7.54 (dd, 1H);

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 10:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-95c690e0c0fe4578a5324883f852bb3f
Source dataset
uspto-grants-2008_01
Patent number
US07323570B2

Reaction notes

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