Triacetoxyperiodinane → 4-Fluoro-3-nitrobenzaldehyde

HRID 58144

Reaction equation

HRID 58144 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 41675874-Fluoro-3-nitrobenzyl alcohol

Product 1

HCID 5981294-Fluoro-3-nitrobenzaldehydeYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-fluoro-3-nitro-phenyl)-methanol (750 g, 4.4 mmol) in DCM (40 mL) at 0° C. was added Dess-Martin Reagent (3.0 g, 7 mmol). The solution was stirred at room temperature for 4 hours. TLC showed disappearance of starting material. The reaction was quenched with 10% NaHCO3 and 10% Na2S2O3 aqueous solution and DCM layer separated and washed with water (100 mL) and brine (50 mL). The reaction was concentrated, and the residue was purified by flash chromatography on silica to obtain the title compound (570 mg, yield: 75%). 1H-NMR (400 MHz, DMSO-d6) δ 10.09 (d, 1H), 8.36 (t, 1H), 8.06 (dd, 1H), 7.97 (m, 1H).

Workup

  1. customThe reaction was quenched with 10% NaHCO3 and 10% Na2S2O3 aqueous solution and DCM layer
  2. customseparated
  3. washwashed with water (100 mL) and brine (50 mL)
  4. concentrationThe reaction was concentrated
  5. customthe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-035f7c5189544f81a4b89988e3a1348d
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Linked notes

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