Triethylsilane → HCID 59557762, compound

HRID 425095Notes

Reaction equation

HRID 425095 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-86f6f404141e4d1aa2cc5c27869b68c3
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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