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

HRID 425040Notes

Reaction equation

HRID 425040 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-898831d6f8054318a764d543467c864b
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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