2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3,4-Difluoro-2-hydroxybenzaldehyde

HRID 602067Notes

Reaction equation

HRID 602067 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([CH2:9][OH:10])[C:3]=1[OH:11].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>ClCCl>[F:1][C:2]1[C:3]([OH:11])=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 451191042,3-Difluoro-6-(hydroxymethyl)phenol

Product 1

HCID 450832693,4-Difluoro-2-hydroxybenzaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2,3-difluoro-6-(hydroxylmethyl)phenol (2.5 g, 15.62 mmol) in dichloromethane (20 mL) was added a suspension of DDQ (5.32 g, 23.43 mmol) in dichloromethane (10 mL) at −5-0° C. The reaction mixture was stirred at room temperature overnight. TLC indicated absence of starting material. Reaction mixture was filtered through a bed of celite and the filtrate was concentrated in vacuum. The crude compound was purified by column chromatography over silica gel using dichloromethane (100%) as eluent to give the aldehyde derivative (2 g, 83% yield) MS: m/z 157 (M+1).

Workup

  1. customReaction mixture
  2. filtrationwas filtered through a bed of celite
  3. concentrationthe filtrate was concentrated in vacuum
  4. customThe crude compound was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-3f9d5525f5da4d12b41889a96652fd15
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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