Lithium Bromide → HCID 63018010, compound

HRID 1992848Notes

Reaction equation

HRID 1992848 reaction equation
CS(O[CH:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[CH2:7][CH3:8])(=O)=O.[Li+].[Br-:19]>CC(C)=O>[CH3:17][O:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][CH:6]([Br:19])[CH2:7][CH3:8])[CH:11]=1

Participants

4

Reactant 2

HCID 82050Lithium Bromide2×HCID 866166461-{[3-(Methyloxy)phenyl]methyl}propyl methanesulfonate

Product 1

HCID 63018010HCID 63018010, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-{[3-(methyloxy)phenyl]methyl}propyl methanesulfonate (52) (4.66 g, 18.0 mmol) in acetone (60 mL) was added LiBr (3.13 g, 36.1 mmol). The reaction mixture was refluxed under nitrogen for 8 h. Another 0.80 g of LiBr was added, and the reflux was continued for 1 h. Cooled to room temperature, the solid was filtered off and washed with acetone. The filtrate was concentrated to give the crude product as a brown oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (100:1) to give 2.07 g (47%) of the title compound (53) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.06 (t, J=7.2 Hz, 3H), 1.70-1.82 (m, 1H), 1.83-1.95 (m, 1H), 3.10-3.20 (m, 2H), 3.80 (s, 3H), 4.10-4.20 (m, 1H), 6.75-6.85 (m, 3H), 7.22 (t, J=7.9 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for 8 h
  2. filtrationthe solid was filtered off
  3. washwashed with acetone
  4. concentrationThe filtrate was concentrated
  5. customto give the crude product as a brown oil
  6. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (100:1)

Sources & evidence

ORD record
ord-e22e6ac45ca4499fab4b54ed6006eb1d
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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