Diethyl Ether → 2-Bromo-4-chlorobenzaldehyde

HRID 252115Notes

Reaction equation

HRID 252115 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Br:12][C:13]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:14]=1[CH2:15][OH:16].C(OCC)C>ClCCl>[Br:12][C:13]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:14]=1[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 54049764(2-Bromo-4-chlorophenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 131547102-Bromo-4-chlorobenzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add pyridinium chlorochromate (432 mg, 2 mmol) to a solution of 2-bromo-4-chlorobenzyl alcohol (200 mg, 0.9 mmol) in dichloromethane (4 mL). Stir the resulting mixture for 2 h. Add diethyl ether (4 mL) and stir for 20-min. Decant the diethyl ether solution. Wash the remaining solids with diethyl ether twice. Combine the diethyl ether solutions and concentrate. Chromatograph on silica gel, eluting with 20:80 to 1:1 ethyl acetate:dichloromethane to give 2-bromo-4-chlorobenzaldehyde as a white solid (167 mg, 85%).

Workup

  1. customDecant the diethyl ether solution
  2. washWash the remaining solids with diethyl ether twice
  3. concentrationconcentrate
  4. washChromatograph on silica gel, eluting with 20:80 to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-1ffc335fca484a58b9ee9b84743ab5b9
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

Loading…