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

HRID 1534907Notes

Reaction equation

HRID 1534907 reaction equation
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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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, 5.0 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.

Workup

  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, 5.0 cm wide column)
  7. washeluting with ER-CX (1:5→1:3)
  8. distillationThe resultant oil was further purified by distillation

Sources & evidence

ORD record
ord-a3b32725507d4da9b94c2235b36cf8ac
Source dataset
uspto-grants-1992_02
Patent number
US05091422

Reaction notes

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