Acetyl chloride → HCID 69518724, compound

HRID 854923Notes

Reaction equation

HRID 854923 reaction equation
[F:1][C:2]([F:19])([F:18])[CH:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4]1.[Al+3].[Cl-].[Cl-].[Cl-].[C:24](Cl)(=[O:26])[CH3:25]>ClCCl>[C:24]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[O:4][CH:3]([C:2]([F:1])([F:18])[F:19])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11]2)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 218835922H-1-Benzopyran-3-carboxylic acid, 2-(trifluoromethyl)-, ethyl ester

Product 1

HCID 69518724HCID 69518724, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL three neck round bottom flask was fitted with stir bar, thermocouple and heating mantle, condenser, and nitrogen inlet and charged with dichloromethane (150 mL), ethyl 2-trifluoromethyl-2H-chromene-3-carboxylate (14.94 g, 54.882 mmole), and AlCl3 (18.29 g, 137.21 mmole). With stirring, the reaction was chilled to 0° C. followed by addition of acetyl chloride (5.85 mL, 6.46 g, 82.32 mmole). The reaction was stirred at RT for three days and then at reflux for six days. The reaction was poured over ice and was extracted with dichloromethane. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to yield a solid. This solid was triturated with hexanes to provide a slurry. Vacuum filtration of the slurry yielded the title compound as a white solid. (11.78 g, 68.3%): mp 101-103° C. 1H NMR (acetone-d6/300 MHz) 8.14(s, 1H), 8.04 (d d, 1H, J=8.7, 2.2 Hz), 7.98(s, 1H), 7.13 (d, 1H, J=8.6 Hz), 5.95 (q, 1H, J=6.8 Hz), 4.38-4.23 (m, 2 H), 2.57(s, 3H), 1.33(t, 3H, J=7.0 Hz). GCMS m/z 314 (M+).

Workup

  1. temperaturethermocouple and heating mantle, condenser, and nitrogen inlet
  2. stirringWith stirring
  3. stirringThe reaction was stirred at RT for three days
  4. temperatureat reflux for six days
  5. additionThe reaction was poured over ice
  6. extractionwas extracted with dichloromethane
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield a solid
  11. customThis solid was triturated with hexanes
  12. customto provide a slurry
  13. filtrationVacuum filtration of the slurry

Sources & evidence

ORD record
ord-3e70a021b8264fa7bd3d0294f60370ea
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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