Triethylamine → HCID 86170301, compound

HRID 2252445Notes

Reaction equation

HRID 2252445 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)(=O)=O.[P:16]([O-:21])([O:19][CH3:20])[O:17][CH3:18].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:13][C:9]1[CH:8]=[C:7]([P:16](=[O:21])([O:19][CH3:20])[O:17][CH3:18])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131552493-Chlorophenyl trifluoromethanesulfonateHCID 21884954Dimethylphosphite

Product 1

HCID 86170301HCID 86170301, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

This reaction was performed using a PersonalChemistry™ microwave instrument set at normal absorbance, fixed hold time and 30 sec pre-stirring. A 10-mL reaction vial was charged with 3-chlorophenyl trifluoromethanesulfonate (0.60 g, 2.30 mmol), dimethyl phosphite (0.42 mL, 4.58 mmol) and triethylamine (0.64 mL, 4.59 mmol) in toluene (4 mL). Nitrogen was bubbled through the stirred solution for 5 min, the tetrakis(triphenylphosphine)palladium(0) (0.1 g) was added, the solution was covered with a blanket of nitrogen and sealed. The reaction mixture was heated 11 min at 160° C., then cooled to room temperature and diluted with ethyl acetate. The yellow solution washed successively with water (3×) and brine. The organic solution was dried over sodium sulfate, filtered and the solvent was removed by rotary evaporation under reduced pressure. Pure dimethyl (3-chlorophenyl)phosphonate was obtained as a colorless oil (0.27 g, 57%) by chromatography over silica gel using ethyl acetate-hexane (gradient: 5% ethyl acetate to 100%). 1H NMR (300 MHz, CDCl3) δ 7.77 (br d, J=13.7 Hz, 1H), 7.68 (ddt, J=13.0, 7.5, 1.4 Hz, 1H), 7.53 (dquint., J=8.0, 1.1 Hz, 1H), 7.38-7.45 (m, 1H), 3.79 (s, 3H), 3.75 (s, 3H) ppm; MS [M+H]+ 221, [2M+H]+ 441

Workup

  1. customhold time and 30 sec
  2. customA 10-mL reaction
  3. customNitrogen was bubbled through the stirred solution for 5 min
  4. additionthe tetrakis(triphenylphosphine)palladium(0) (0.1 g) was added
  5. customsealed
  6. temperaturecooled to room temperature
  7. additiondiluted with ethyl acetate
  8. washThe yellow solution washed successively with water (3×) and brine
  9. dry with materialThe organic solution was dried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvent was removed by rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-d1b0b0eff0704694adc75a247b719b1c
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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