Diethyl Ether → 2-(2-Bromophenyl)acetaldehyde

HRID 652005Notes

Reaction equation

HRID 652005 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]=[O:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27340892-(2-Bromophenyl)ethan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 114241802-(2-Bromophenyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9.11 grams (0.045 mole) of 2-(2-bromophenyl)ethanol in 35 milliliters of methylene chloride was added to a stirred suspension of 14.62 grams (0.063 mole) of pyridinium chlorochromate in 75 milliliters of methylene chloride at ambient temperature whereupon a slightly exothermic reaction took place with the formation of a black reaction mixture. Stirring was continued for 15 hours at ambient temperature; then 150 milliliters of ether was added and the mixture filtered through silica gel on a pad of celite. The insoluble residue was washed with 100 milliliters of ether, filtered, the ether solutions combined and the solvents evaporated on a rotary evaporator to recover as residue, 8.0 grams (90 percent) of the desired 2-(2-bromophenyl)acetaldehyde intermediate as an oil. The oil had an Rf of 0.6 on silica gel when eluted with one percent methanol in chloroform.

Workup

  1. filtrationthe mixture filtered through silica gel on a pad of celite
  2. washThe insoluble residue was washed with 100 milliliters of ether
  3. filtrationfiltered
  4. customthe solvents evaporated on a rotary evaporator
  5. customto recover as residue
  6. washeluted with one percent methanol in chloroform

Sources & evidence

ORD record
ord-b2525f8437c94b5b999783693b4d4a5f
Source dataset
uspto-grants-1987_06
Patent number
US04670443

Reaction notes

Loading…