1-Bromo-3-chloropropane → 5-Chloro-2-(2-trifluoromethylphenyl)pentanenitrile

HRID 546795

반응식

HRID 546795 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].CC(C)([O-])C.[K+].Br[CH2:21][CH2:22][CH2:23][Cl:24]>C1COCC1>[Cl:24][CH2:23][CH2:22][CH2:21][CH:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:12])([F:13])[F:1])[C:10]#[N:11]

참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 764352-(Trifluoromethyl)phenylacetonitrileHCID 23665647Potassium tert-butoxide

생성물 1

HCID 668395985-Chloro-2-(2-trifluoromethylphenyl)pentanenitrile수율 132%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

(2-Trifluoromethylphenyl)acetonitrile (12.47 g, 67.3 mmol) was dissolved in THF (87.3 mL) at room temperature under nitrogen atmosphere. The reaction solution was cooled to −10° C. Then, potassium tert-butoxide (7.93 g, 70.7 mmol) was added to the reaction solution and the reaction mixture was stirred at −10° C. for 10 minutes. 1-Bromo-3-chloropropane (6.99 mL, 70.7 mmol) was added dropwise to the reaction mixture over 14 minutes, and the reaction mixture was stirred at 0° C. for 2 hours. The reaction was quenched with 10% NH4Cl aq. (8.6 mL). After the mixture was stirred, the aqueous layer was separated. The organic layer was concentrated under the reduced pressure to obtain the title compound (23.24 g). The yield was calculated as over 99% by HPLC external standard method.

후처리

  1. stirringthe reaction mixture was stirred at 0° C. for 2 hours
  2. customThe reaction was quenched with 10% NH4Cl aq. (8.6 mL)
  3. stirringAfter the mixture was stirred
  4. customthe aqueous layer was separated
  5. concentrationThe organic layer was concentrated under the reduced pressure

출처 및 근거

ORD 기록
ord-d045f116488943008215e35a9e10d823
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935815B2

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