Triethylsilane → HCID 59557762, compound

HRID 2403772Notes

Reaction equation

HRID 2403772 reaction equation
[SiH](CC)(CC)CC.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:27])=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][Br:26])=[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:27])=[C:13]([CH2:15][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][Br:26])=[CH:19][CH:18]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 12052Triethylsilane2×HCID 62406Trifluoromethanesulfonic acidHCID 59557776HCID 59557776, compound

Product 1

HCID 59557762HCID 59557762, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of Et3SiH (1.4 mL, 8.50 mmol) and (5-bromo-2-chlorophenyl)(4-(3-bromopropyl)phenyl)methanone (2.36 g, 5.67 mmol) in TFA (10 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 stirring for 2.5 h, additional Et3SiH (0.45 mL, 2.85 mmol) was added and the mixture was heated to 50° C. After stirring for 4.5 h the reaction was complete, and 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 water, 2× with aqueous Na2CO3 and 2× with brine, and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the residue (2.3 g) was used in the next step without further purification.

Workup

  1. temperatureWithin a few minutes the temperature of the solution increased
  2. temperatureto reflux violently
  3. stirringAfter stirring for 4.5 h the reaction
  4. customthe volatiles were removed under reduced pressure
  5. additionThe residue was poured into brine
  6. extractionextracted 3× with ethyl acetate
  7. washThe combined organic layers were washed 3× with water, 2× with aqueous Na2CO3 and 2× with brine
  8. dry with materialdried over Na2SO4
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue (2.3 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-73f8f0326efc4aa39c56f9d013217d0c
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

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