Triethylsilane → 4-Bromo-2-(4-(bromomethyl)benzyl)-1-chlorobenzene

HRID 2403717Notes

Reaction equation

HRID 2403717 reaction equation
[SiH](CC)(CC)CC.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:25])=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][Br:24])=[CH:19][CH:18]=2)=O)[CH:14]=1.C(S(O)(=O)=O)(F)(F)F>C(O)(C(F)(F)F)=O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:25])=[C:13]([CH2:15][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][Br:24])=[CH:19][CH:18]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 59557730HCID 59557730, compound

Product 1

HCID 595577434-Bromo-2-(4-(bromomethyl)benzyl)-1-chlorobenzene

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of Et3SiH (17 mL) and (5-bromo-2-chlorophenyl)(4-(bromomethyl)phenyl)methanone (intermediate AH) (20.75 g, 54 mmol) in TFA (100 mL) at 30° C. was added CF3SO3H (0.05 mL). Within a few minutes the temperature of the solution increased causing it to reflux violently. After 3 h, the volatiles were removed under reduced pressure. The residue was poured into brine and extracted 3× with ethyl acetate. The combined organic layers were washed 3× with H2O, 2× with aqueous Na2SO4 and 2× with brine, and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the product was purified by column chromatography to obtain pure intermediate AI (15.5 g).

Workup

  1. temperatureWithin a few minutes the temperature of the solution increased
  2. temperatureto reflux violently
  3. customthe volatiles were removed under reduced pressure
  4. additionThe residue was poured into brine
  5. extractionextracted 3× with ethyl acetate
  6. washThe combined organic layers were washed 3× with H2O, 2× with aqueous Na2SO4 and 2× with brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was evaporated under reduced pressure
  9. customthe product was purified by column chromatography
  10. customto obtain pure intermediate AI (15.5 g)

Sources & evidence

ORD record
ord-95faa097e2904118ac17088153f58f4d
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

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