Bromoacetonitrile → Ethyl 2,2-bis(4-chlorophenyl)-3-cyanopropanoate

HRID 2408850노트

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HRID 2408850 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:32][C:33]#[N:34]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)([CH2:32][C:33]#[N:34])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 11534BromoacetonitrileHCID 101291Benzeneacetic acid, 4-chloro-alpha-(4-chlorophenyl)-, ethyl esterHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 67387582Ethyl 2,2-bis(4-chlorophenyl)-3-cyanopropanoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

Ethyl 2,2-bis(4-chlorophenyl)acetate (5.50 g, 17.8 mmol) was dissolved in 100 mL of dry tetrahydrofuran and cooled to −78° C. Lithium bis(trimethylsilyl)amide (1.0 M in hexane, 18.0 mL, 18.0 mmol) was added dropwise via syringe under nitrogen. The reaction was brought to 0° C., stirred for 1 hour, and then cooled to −78° C. A solution of bromoacetonitrile (1.24 mL, 17.8 mmol) dissolved in tetrahydrofuran was added, and the reaction was stirred for 2 hours while warming to room temperature. The reaction was quenched with saturated NH4Cl solution and extracted with diethyl ether. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated. Chromatography on silica gel (Analogix Intelliflash 280; 10% ethyl acetate/hexane) yielded the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 7.38-7.32 (m, 4H), 7.22-7.17 (m, 4H), 4.25 (q, J=7.2, 2H), 3.32 (s, 2H), 1.23 (t, J=7.2, 3H); MS (DCI+) m/z 365 (M+NH4)+.

후처리

  1. customwas brought to 0° C.
  2. temperaturecooled to −78° C
  3. additionwas added
  4. stirringthe reaction was stirred for 2 hours
  5. temperaturewhile warming to room temperature
  6. customThe reaction was quenched with saturated NH4Cl solution
  7. extractionextracted with diethyl ether
  8. washThe organic phase was washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8ff1763dee7448c89d898807d294e7ea
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815869B2

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