Ethyl Acetate → (2-Bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol

HRID 1716957Notes

Reaction equation

HRID 1716957 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([C:12](=O)[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([Cl:22])=[CH:8][C:3]=1[C:4](OC)=[O:5].C([SiH](CC)CC)C.FC(F)(F)S(O)(=O)=O.C(OCC)(=O)C>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)[C:9]([Cl:22])=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 59557708HCID 59557708, compound

Product 1

HCID 59467877(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of methyl 2-bromo-5-chloro-4-(4-ethylbenzoyl)benzoate (7.64 g, 20 mmol) in 2,2,2-trifluoroacetic acid (38 mL) was added to triethylsilane (5.88 mL, 40 mmol) under argon. After it was stirred for 10 min at room temperature, trifluoromethanesulfonic acid (0.1 mL) was added. The reaction temperature was raised from 26° C. to reflux. After stirring for 2 hours, TLC (petroleum ether:ethyl acetate=6:1, Rf=0.7) showed the reaction was complete. The reaction mixture was evaporated and the residue was dissolved in ethyl acetate (150 mL). The organic layer was washed 2× with H2O, 2× with NaHCO3, and 2× with brine, dried over anhydrous Na2SO4. Concentration under reduced pressure provided the title compound as a white solid. Yield: 7.2 g (100%). 1H NMR (CDCl3, 300 MHz) δ 7.85 (s, 1H), 7.44 (s, 1H), 7.17 (s, 1H), 7.14 (s, 1H), 7.10 (s, H), 7.07 (s, 1H), 4.05 (s, 2H), 3.92 (s, 3H), 2.63 (q, J=7.8 Hz, 2H), 1.24 (t, J=7.8 Hz, 3H).

Workup

  1. temperatureThe reaction temperature was raised from 26° C.
  2. temperatureto reflux
  3. stirringAfter stirring for 2 hours
  4. customThe reaction mixture was evaporated
  5. dissolutionthe residue was dissolved in ethyl acetate (150 mL)
  6. washThe organic layer was washed 2× with H2O, 2× with NaHCO3, and 2× with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-3c2086a92527424eae4d2dc959589ca2
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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