2-(3-Butoxyphenyl)-2-fluoroacetonitrile → HCID 71152226, 화합물

HRID 62598노트

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HRID 62598 반응식
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]([F:15])[C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]>C1COCC1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]([F:15])[CH2:13][NH2:14])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

3

반응물 1

HCID 711520922-(3-Butoxyphenyl)-2-fluoroacetonitrile

생성물 1

HCID 71152226HCID 71152226, 화합물수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 2-(3-butoxyphenyl)-2-fluoroacetonitrile (109 mg: 0.53 mmol) in dry THF (5 mL), borane tetrahydrofurane complex (2.10 mL; 2.10 mmol) is added and the reaction is stirred at 0° C. for 2 hours and then at RT for 6 hours. An LC/MS shows almost complete conversion. The reaction is quenched adding slowly few drops of EtOH and few drops of conc. HCl/EtOH (1:5) and stirring is continued for 5 min. DCM was then added, followed by 5% aqueous NaHCO3. The two phases are separated and the aqueous phase is extracted twice with DCM. The combined organic layers are dried over Na2SO4, filtered and evaporated. The crude residue is purified using a SCX cartridge (eluant: DCM/MeOH 1/1 to MeOH/conc. aq. NH3 95/5) affording 2-(3-butoxyphenyl)-2-fluoroethanamine (92 mg; 0.43 mmol; 83%) as a pale yellow oil.

후처리

  1. waitat RT for 6 hours
  2. customThe reaction is quenched
  3. additionadding slowly few drops of EtOH and few drops of conc. HCl/EtOH (1:5)
  4. stirringstirring
  5. waitis continued for 5 min
  6. additionDCM was then added
  7. customThe two phases are separated
  8. extractionthe aqueous phase is extracted twice with DCM
  9. dry with materialThe combined organic layers are dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated
  12. customThe crude residue is purified

출처 및 근거

ORD 기록
ord-32d03c35920f43cb80f45eda232504c2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447029B2

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