Water → 5-(2,2,2-Trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzaldehyde

HRID 2269244Notes

Reaction equation

HRID 2269244 reaction equation
[F:1][C:2]([F:17])([F:16])[CH:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:4]([F:7])([F:6])[F:5].[CH:18]([O:21]C)(Cl)Cl.O>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[F:1][C:2]([F:16])([F:17])[CH:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([CH:9]=1)[CH:18]=[O:21])[C:4]([F:6])([F:5])[F:7]

Participants

6

Reactant 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 183336204-(2,2,2-Trifluoro-1-(trifluoromethyl)ethyl)anisole

Product 1

HCID 186776145-(2,2,2-Trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzaldehydeYield 90.9%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred and ice-cooled solution of Compound 8 (650 mg, 2.5 mmol) in dry CH2Cl2 (15 ml) was added neat TiCl4 (950 mg, 5.0 mmol) followed by Cl2CHOMe (600 mg, 5.0 mmol). After the addition was complete, the mixture was stirred at room temperature for 5 hr, poured into H2O (60 ml), and extracted with CH2Cl2. The combined extracts were dried (Na2SO4), and concentrated in vacuo to give a yellow oil, which was purified by a column chromatography on silica gel to give Compound 9 (650 mg, 90%)

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for 5 hr
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil, which
  7. customwas purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-775882272a5847b1b8636a5059b798c2
Source dataset
uspto-grants-2001_12
Patent number
US06329396B1

Reaction notes

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