Lithium Bromide → 1-(2-Bromopropyl)-3-methoxybenzene

HRID 1992810Notes

Reaction equation

HRID 1992810 reaction equation
CS(O[CH:6]([CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)(=O)=O.[Li+].[Br-:18]>CC(C)=O>[Br:18][CH:6]([CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 866166351-Methyl-2-[3-(methyloxy)phenyl]ethyl methanesulfonate

Product 1

HCID 630181851-(2-Bromopropyl)-3-methoxybenzeneYield 100.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A round-bottomed flask was charged with 1-methyl-2-[3-(methyloxy)phenyl]ethyl methanesulfonate (2) (90 g, 0.368 mol), LiBr (80 g, 0.92 mol), and acetone (650 mL). The reaction mixture was refluxed for 24 h under N2 and then cooled to room temperature. The reaction mixture was filtered and concentrated under reduced pressure to afford the crude product. The product was passed through a pad of silica gel to remove inorganic impurities. The product was distilled under reduced pressure (2-3 mm Hg) at 130-135° C. to afford ˜85 g (100%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 7.25 (dd, J1=8.00 Hz, J2=8.00 Hz, 1H), 6.84-6.78 (m, 3H), 4.32 (sextet, J=4.00 Hz, 1H), 3.82 (s, 3H), 3.25 and 3.21 (dd, J1=16.00 Hz, J2=8.00 Hz, 1H), 3.07 and 3.04 (dd, J1=16.00 Hz, J2=8.00 Hz, 1H), 1.71 (d, J=8.00 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h under N2
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. customto remove inorganic impurities
  6. distillationThe product was distilled under reduced pressure (2-3 mm Hg) at 130-135° C.

Sources & evidence

ORD record
ord-d4db4b79dc5c4a44bae092713b578191
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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