Chloroiodomethane → 2-(2-(Trifluoromethyl)phenyl)oxirane

HRID 2062

반응식

HRID 2062 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[C:4]([CH:9]=[O:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.I[CH2:14]Cl.C[Li]>O1CCCC1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][O:10]1

참가 물질

5

반응물 3

HCID 11644ChloroiodomethaneHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 139032672-(2-(Trifluoromethyl)phenyl)oxirane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

α,α,α-trifluoro-o-tolualdehyde (3 g) was dissolved in anhydrous tetrahydrofuran and cooled to -78° C., iodochloromethane (1.38 ml) was then added, followed by methyllithium (1.5M complexed with lithium bromide) (12 ml) added over 5 minutes. The reaction was left to warm up to room temperature overnight. The reaction was quenched using saturated ammonium chloride solution and extracted using diethyl ether (2×50 ml). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to afford a brown oil. Purification on flash silica eluted with 100% hexane up to 5% EtOAC in hexane afforded a colourless oil (1.1 g). 1H NMR (250 MHz, CDCl3) δ2.61-2.71 (1H, dd), 3.14-3.25 (1H, dd), 4.17-4.27 (1H, m), 7.33-7.70 (5H, m).

후처리

  1. additionadded over 5 minutes
  2. waitThe reaction was left
  3. temperatureto warm up to room temperature overnight
  4. customThe reaction was quenched
  5. extractionextracted
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto afford a brown oil
  10. customPurification on flash silica
  11. washeluted with 100% hexane up to 5% EtOAC in hexane

출처 및 근거

ORD 기록
ord-622fcecd2a0b4607a07fac649d6051df
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728695

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