Chlorotrimethylsilane → HCID 57475109, 화합물

HRID 1948602노트

반응식

HRID 1948602 반응식
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

참가 물질

9

반응물 5

HCID 6397ChlorotrimethylsilaneHCID 140821-Bromo-3-fluorobenzeneHCID 25517Ammonium ChlorideHCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 5462224Magnesium2회

생성물 1

HCID 57475109HCID 57475109, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매3회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-46a04ba79a9741adba37e662e56cfb3f
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399503B2

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