Acetyl chloride → HCID 67305077, compound

HRID 1009171Notes

Reaction equation

HRID 1009171 reaction equation
[F:1][C:2]([F:12])([F:11])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.FC(F)(F)S(O)(=O)=O.[C:21](Cl)(=[O:23])[CH3:22].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C:2]([F:11])([F:12])[F:1])=[CH:5][C:6]=1[C:21](=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 62406Trifluoromethanesulfonic acidHCID 6451240Aluminum(III) ChlorideHCID 224853604-(2,2,2-Trifluoroethyl)phenol

Product 1

HCID 67305077HCID 67305077, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
150 °C

Procedure

To a solution of 4-(2,2,2-trifluoroethyl)phenol (1.00 g, 5.68 mmol) in CH2Cl2 (5.0 ml) was added trifluoromethanesulfonic acid (0.0151 ml, 0.170 mmol) with stirring. A solution of acetic chloride (0.444 ml, 6.25 mmol) in CH2Cl2 (5.0 ml) was added drop wise to the reaction. After stirred 45 min at RT, all the phenol was consumed. The product mixture was diluted with CH2Cl2, washed with saturated sodium bicarbonate. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum until no weight loss was observed. To the above residue was added anhydrous aluminum(III) chloride (0.757 g, 5.68 mmol). The mixture was heated at 150° C. for 1 h until all the starting material was consumed (monitored by TLC). The resulted brown gum was cooled to 0° C., diluted with diethyl ether and 1N HCl. Layers were separated. The aqueous layer was extracted with ether. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (2-15% EtOAc/hexane) to afford the title compound.

Workup

  1. customwise to the reaction
  2. stirringAfter stirred 45 min at RT
  3. customall the phenol was consumed
  4. additionThe product mixture was diluted with CH2Cl2
  5. washwashed with saturated sodium bicarbonate
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was dried in vacuum until no weight loss
  10. customwas consumed (monitored by TLC)
  11. temperatureThe resulted brown gum was cooled to 0° C.
  12. additiondiluted with diethyl ether and 1N HCl
  13. customLayers were separated
  14. extractionThe aqueous layer was extracted with ether
  15. dry with materialdried over Na2SO4
  16. filtrationfiltered
  17. concentrationconcentrated
  18. customThe residue was purified on silica gel column (2-15% EtOAc/hexane)

Sources & evidence

ORD record
ord-12e85c5284114715b8efc36c8b079384
Source dataset
uspto-grants-2011_07
Patent number
US07973047B2

Reaction notes

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