Lithium Bromide → 1-(2-Bromo-ethoxymethyl)-4-chlorobenzene

HRID 2261246Notes

Reaction equation

HRID 2261246 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][CH2:8][CH2:9]OS(C)(=O)=O)=[CH:4][CH:3]=1.[Br-:17].[Li+]>CC(C)=O>[Br:17][CH2:9][CH2:8][O:7][CH2:6][C:5]1[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 59593471Methanesulfonic acid 2-(4-chloro-benzyloxy)-ethyl ester2×

Product 1

HCID 136543741-(2-Bromo-ethoxymethyl)-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methanesulfonic acid 2-(4-chloro-benzyloxy)-ethyl ester (Intermediate 6) (1.37 g, 5.18 mmol) and lithium bromide (1.80 g, 20.7 mmol) in acetone (15 mL) was heated at reflux overnight. The reaction mixture was concentrated to dryness and the residue partitioned between DCM and water. The organic layer was dried (MgSO4), and concentrated, and purified by column chromatography over silica using DCM/cyclohexane (1:3) as eluent to afford the product as a colourless oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customthe residue partitioned between DCM and water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by column chromatography over silica

Sources & evidence

ORD record
ord-59ca3905a1594c12915c5fbac4032272
Source dataset
uspto-grants-2010_12
Patent number
US07846955B2

Reaction notes

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