Chlorotrimethylsilane → HCID 57475109, compound

HRID 1948602Notes

Reaction equation

HRID 1948602 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[CH:3]=1.[Mg].[CH3:10][N:11]([CH3:24])[C:12]1(C#N)[CH2:21][CH2:20][C:15]2([O:19][CH2:18][CH2:17][O:16]2)[CH2:14][CH2:13]1.[NH4+].[Cl-].[Cl:27][Si](C)(C)C>CCOCC.C1COCC1.O>[ClH:27].[F:8][C:4]1[CH:3]=[C:2]([C:12]2([N:11]([CH3:24])[CH3:10])[CH2:21][CH2:20][C:15]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:14][CH2:13]2)[CH:7]=[CH:6][CH:5]=1

Participants

9

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 140821-Bromo-3-fluorobenzeneHCID 25517Ammonium ChlorideHCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 5462224Magnesium2×

Product 1

HCID 57475109HCID 57475109, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-bromo-3-fluorobenzene (5.00 g, 28.6 mmole) in absolute ether (15 ml) was added dropwise to a suspension of magnesium (694 mg, 28.6 mmole) in absolute ether (10 ml) at such a rate that the ether boiled. After completion of the addition the reaction mixture was stirred for 10 minutes at RT, following which the magnesium had completely dissolved. The reaction solution was cooled in an ice bath and 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (3.00 g, 14.3 mmole) in absolute THF (30 ml) was added dropwise at 10° C. The reaction mixture was stirred at room temperature overnight, 20% NH4Cl-solution (20 ml) and water (30 ml) were added thereto while cooling with ice, and the mixture was extracted with ether (3×50 ml). The organic phase was washed with water (50 ml) and then with saturated NaCl solution (50 ml), dried over Na2SO4 and concentrated by evaporation in vacuo. The crude product was dissolved in ethyl methyl ketone (25 ml), ClSiMe3 (3.2 ml, 25 mmole) was added while cooling with ice, and the mixture was stirred at room temperature for 5 hours. The precipitate formed was filtered off and dried in vacuo.

Workup

  1. additionAfter completion of the addition the reaction mixture
  2. dissolutionhad completely dissolved
  3. temperatureThe reaction solution was cooled in an ice bath
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. temperaturewhile cooling with ice
  6. extractionthe mixture was extracted with ether (3×50 ml)
  7. washThe organic phase was washed with water (50 ml)
  8. dry with materialwith saturated NaCl solution (50 ml), dried over Na2SO4
  9. concentrationconcentrated by evaporation in vacuo
  10. dissolutionThe crude product was dissolved in ethyl methyl ketone (25 ml)
  11. temperaturewhile cooling with ice
  12. stirringthe mixture was stirred at room temperature for 5 hours
  13. customThe precipitate formed
  14. filtrationwas filtered off
  15. customdried in vacuo

Sources & evidence

ORD record
ord-46a04ba79a9741adba37e662e56cfb3f
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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