Dimethyl Sulfoxide → 4-(3,3,4,4,5,5,6,6,6-Nonafluorohexyl)benzaldehyde

HRID 1046287Notes

Reaction equation

HRID 1046287 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]([F:33])([C:23]([F:32])([F:31])[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[F:11][C:12]([F:33])([C:23]([F:31])([F:32])[C:24]([F:30])([F:29])[C:25]([F:26])([F:27])[F:28])[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]=[O:22])=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 16211129[4-(3,3,4,4,5,5,6,6,6-Nonafluorohexyl)phenyl]methanol

Product 1

HCID 866134394-(3,3,4,4,5,5,6,6,6-Nonafluorohexyl)benzaldehydeYield 40.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of oxalyl chloride (80.2 μL, 0.93 mmol) in dichloromethane (8 mL) at −78° C., dimethyl sulfoxide (132.2 μL, 1.86 mmol) was added dropwise. After 15 minutes, 4-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)benzenemethanol (300 mg, 0.85 mmol) was added. After 30 minutes, triethylamine (590 μL, 4.23 mmol) was added. The reaction was then allowed to warm to room temperature. Saturated sodium bicarbonate solution was added. The mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 122 mg of 4-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)benzaldehyde; 1H NMR (300 MHz, CDCl3) δ 10.00 (s, 1H), 7.85 (d, 2H), 7.40 (d, 2H), 3.01 (m, 2H), 2.41 (m, 2H) ppm.

Workup

  1. waitAfter 30 minutes
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-24dce68d6e0a49c7946c4ce8b5051a62
Source dataset
uspto-grants-2013_10
Patent number
US08569303B2

Reaction notes

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