Sodium Chloride → 3-(2-Chloro-6-fluorophenyl)propanal

HRID 408489Notes

Reaction equation

HRID 408489 reaction equation
S(=O)(=O)=O.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[CH2:13][CH2:14][CH2:15][OH:16].C(N(CC)CC)C.[Cl-].[Na+]>CS(C)=O.ClCCl>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:7]=1[CH2:13][CH2:14][CH:15]=[O:16]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 24682Sulfur trioxideHCID 282970863-(2-Chloro-6-fluorophenyl)propan-1-ol

Product 1

HCID 282762173-(2-Chloro-6-fluorophenyl)propanalYield 74%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of pyridine complex with sulfur trioxide (40.35 g, 0.225 mol) in dimethylsulfoxide (50 mL) was slowly added to a solution of 3-(2-chloro-6-fluoro-phenyl)-propan-1-ol (20.6 g, 0.109 mol) and triethylamine (25.8 g, 0.225 mol) in dichloromethane (250 mL) at 0° C. The reaction was allowed to stir for 30 minutes, and then it was poured into a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The combined organic layers were washed twice with water and then with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to dryness. The crude product was purified by silica gel chromatography to afford 3-(2-Chloro-6-fluoro-phenyl)-propionaldehyde (15 g, 80 mmol, 74%), 1H NMR (CDCl3): δ 9.83 (s, 1H), 7.24-7.00 (m, 2H), 6.99-6.94 (m, 1H), 3.13-3.09 (m, 2H), 2.75-2.71 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed twice with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-031ab3e590534e6fac0255f64ee963a2
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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