Water → 2-Chloro-3-(trifluoromethyl)benzaldehyde

HRID 1096833Notes

Reaction equation

HRID 1096833 reaction equation
[Li]CCCC.[F:6][C:7]([F:16])([F:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14].CN([CH:20]=[O:21])C.O>C1COCC1>[Cl:14][C:9]1[C:8]([C:7]([F:6])([F:15])[F:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH:20]=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 69211-Chloro-2-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 27366722-Chloro-3-(trifluoromethyl)benzaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

BuLi (1.6 M in hexane, 173 mL, 277 mmol) was added to a sol. of 2-trifluoromethyl-chlorobenzene (50.0 g, 277 mmol) in THF (500 mL) at −70° C. The sol. was stirred for 2 h at −70° C., and DMF (21.3 mL, 277 mmol) in THF (100 mL) was added. The mixture was allowed to warm to rt overnight. Water was added (200 mL), and the mixture was extracted with Et2O (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane/EtOAc 20:1) yielded the title compound (37.4 g, 65%). LC-MS: tR=0.96 min.

Workup

  1. temperatureto warm to rt overnight
  2. extractionthe mixture was extracted with Et2O (2×)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (heptane/EtOAc 20:1)

Sources & evidence

ORD record
ord-43cb4c74db514d84b642b57af4708b1f
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

Loading…