Water → 4-Bromo-2-(trifluoromethyl)benzaldehyde

HRID 415998Notes

Reaction equation

HRID 415998 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Br)Br)=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.C1C[O:18]CC1.O>[N+]([O-])([O-])=O.[Ag+].C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:18])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 59474514Benzene, 4-bromo-1-(dibromomethyl)-2-(trifluoromethyl)-

Product 1

HCID 121872184-Bromo-2-(trifluoromethyl)benzaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Combine 4-bromo-1-(dibromomethyl)-2-(trifluoromethyl)benzene (6.66 g, 16.8 mmol), silver nitrate (14.8 g, 87.3 mmol), THF (250 mL), and water (35 mL) in a 500 mL flask equipped with a magnetic stir bar, reflux condenser, and N2 inlet. Reflux the mixture while stirring for 2.5 hours then cool to room temperature. Filter the reaction through Celite®, add ethyl acetate (250 mL) and wash with water (2×200 mL) then saturated aqueous sodium chloride solution (1×200 mL). Dry over anhydrous magnesium sulfate, concentrate to an orange oil, and purify the crude product via silica gel chromatography eluting with hexanes to afford 3.46 g (81%) of the product as a clear oil: 1H NMR (300 MHz, CDCl3) δ 10.35-10.33 (m, 1H), 8.0 (d, 1H, J=8.3 Hz), 7.93 (d, 1H, J=1.4 Hz), 7.86 (dd, 1H, J=1.2 Hz, J=8.3 Hz).

Workup

  1. temperaturereflux condenser, and N2 inlet
  2. temperatureReflux the mixture
  3. filtrationFilter
  4. customthe reaction through Celite®
  5. washwash with water (2×200 mL)
  6. dry with materialDry over anhydrous magnesium sulfate
  7. concentrationconcentrate to an orange oil
  8. custompurify the crude product via silica gel chromatography
  9. washeluting with hexanes

Sources & evidence

ORD record
ord-4ce2748c2c844cc4a61beb76d4189b03
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

Loading…