Methanol → 2-Chloro-5-(trifluoromethoxy)benzaldehyde

HRID 1267895Notes

Reaction equation

HRID 1267895 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH:13]=C.C[OH:16]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH:13]=[O:16]

Participants

4

Reactant 2

HCID 887MethanolHCID 185425101-Chloro-2-ethenyl-4-(trifluoromethoxy)benzene

Product 1

HCID 185425172-Chloro-5-(trifluoromethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloro-2-vinyl-4-(trifluoromethoxy)benzene (Description 26; 274 mg, 1.2 mmol) was dissolved in dichloromethane (15 mL) and methanol (5 mL) and the solution cooled to −78° C. Ozone was then bubbled through until the solution turned blue. Dimethyl sulfide (1 mL) was added and the solution allowed to stir to ambient temperature for 16 hours. Concentration yielded an oil which was purified by silica chromatography to give the title compound (120 mg, 0.53 mmol).

Workup

  1. customOzone was then bubbled through until the solution
  2. additionDimethyl sulfide (1 mL) was added
  3. concentrationConcentration
  4. customyielded an oil which
  5. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-ce7fb8aa4fbb4605b63e36e3effef116
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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