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

HRID 5216

反応式

HRID 5216 の反応式
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

参加物

7

反応物 5

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

生成物 1

HCID 137472413-(4-Fluorophenyl)propan-1-ol収率 51.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-818d644ce64a41d8816409c37119191b
出典データセット
uspto-grants-1993_09
特許番号
US05243076

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