Iodine → 3-(4-Fluorophenyl)propan-1-ol

HRID 5216

반응식

HRID 5216 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Mg].II.[O:12]1[CH2:15][CH2:14][CH2:13]1.[NH4+].[Cl-]>C1COCC1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:15][CH2:14][CH2:13][OH:12])=[CH:3][CH:4]=1

참가 물질

7

반응물 5

HCID 807IodineHCID 99931-Bromo-4-fluorobenzeneHCID 10423OxetaneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

생성물 1

HCID 137472413-(4-Fluorophenyl)propan-1-ol수율 51.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A Grignard reagent was prepared from 4-bromo-1-fluorobenzene (8.0 g)., magnesium turnings (1.10 g), and iodine (one small crystal) in THF (40 ml). Oxetane (2.3 g) in THF (10 ml) was added at RT and the reaction mixture was heated at reflux overnight. The cooled solution was poured into aqueous saturated NH4Cl (100 ml), extracted with ER (2×150 ml) and the combined, dried (Na2SO4) extracts were evaporated. The residual oil was purified by flash chromatography over silica gel (Merck 9285, 0.5 cm wide column), eluting with ER- CX (1:5→1:3). The resultant oil was further purified by distillation to give the title compound (3.15 g) as a colourless oil, b.p. 150°/0.8 torr.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. extractionextracted with ER (2×150 ml)
  4. dry with materialdried (Na2SO4) extracts
  5. customwere evaporated
  6. customThe residual oil was purified by flash chromatography over silica gel (Merck 9285, 0.5 cm wide column)
  7. washeluting with ER- CX (1:5→1:3)
  8. distillationThe resultant oil was further purified by distillation

출처 및 근거

ORD 기록
ord-818d644ce64a41d8816409c37119191b
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05243076

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