Lithium Bromide → 4-(2-Bromoethyl)oxane

HRID 1010945

Reaction equation

HRID 1010945 reaction equation
CS(O[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)(=O)=O.[Br-:14].[Li+]>CC(C)=O>[Br:14][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 222730832-(Tetrahydro-2H-pyran-4-yl)ethyl methanesulfonate

Product 1

HCID 226370124-(2-Bromoethyl)oxaneYield 69.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 2-(tetrahydro-2H-pyran-4-yl)ethyl methanesulfonate (5.4 g) in dry acetone at room temperature was added lithium bromide (9 g) in one go. The reaction was heated to reflux for 4 hours, under nitrogen. The reaction was cooled to room temperature and concentrated in vacuo. The residue was taken up in dichloromethane (100 ml) and washed with water (50 ml). The organic layer was dried by passing through a hydrophobic frit, and concentrated in vacuo. The product was purified by silica chromatography (40 g) (ISCO) using a gradient elution of 0-50% cyclohexane:ethyl acetate to afford the title compound as a colourless oil (3.5 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 hours, under nitrogen
  3. concentrationconcentrated in vacuo
  4. washwashed with water (50 ml)
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by silica chromatography (40 g) (ISCO)
  8. washa gradient elution of 0-50% cyclohexane

Sources & evidence

ORD record
ord-886c78ff6a324304b1d02e82947b120c
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Linked notes

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