Triethylamine → 3-Methyl-4'-trifluoromethyl-biphenyl-4-carbaldehyde

HRID 1669240Notes

Reaction equation

HRID 1669240 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].CCN(CC)CC.C1C=CN=CC=1.O=S(=O)=O>CS(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 22280004[3-Methyl-4'-(trifluoromethyl)biphenyl-4-yl]methanol

Product 1

HCID 597293813-Methyl-4'-trifluoromethyl-biphenyl-4-carbaldehydeYield 76.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (3-methyl-4′-trifluoromethyl-biphenyl-4-yl)-methanol (1.613 g, 6.060 mmol) in dimethylsulfoxide (DMSO, 12.0 mL) is treated with Et3N (5.50 mL, 39.460 mmol) and pyridine-sulfur trioxide (2.902 g, 18.235 mmol) in a cold water bath. The bath is removed after 3 min. and the reaction is stirred overnight. The reaction mixture is poured into H2O (50 mL) and extracted with EtOAc (3×50 mL). Combined organic extracts are dried over MgSO4, filtered, and conc. The residue is loaded onto silica gel and eluted with hexanes using a gradient from 5% EtOAc to 33% EtOAc to provide 3-methyl-4′-trifluoromethyl-biphenyl-4-carbaldehyde (1.221 g, 76%) as white crystals.

Workup

  1. customThe bath is removed after 3 min.
  2. additionThe reaction mixture is poured into H2O (50 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialCombined organic extracts are dried over MgSO4
  5. filtrationfiltered
  6. washeluted with hexanes using a gradient from 5% EtOAc to 33% EtOAc

Sources & evidence

ORD record
ord-fba602de18074754a904910037e946a0
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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