Dimethyl Sulfoxide → HCID 20468877, compound

HRID 1388889Notes

Reaction equation

HRID 1388889 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:10]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=[O:12].CS(C)=[O:27]>>[Cl:24][C:21]1[CH:22]=[CH:23][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:2]=[O:27])=[C:10]([C:11](=[O:12])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[CH:20]=1

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 12834647HCID 12834647, compound

Product 1

HCID 20468877HCID 20468877, compound

Procedure

The starting material is prepared as follows: The solution of 3.2 g of 2-(o-bromomethylphenyl)-5-chloro-2'-fluorobenzophenone in 40 ml of freshly distilled dimethylsulfoxide is heated for 30 minutes in an oil bath at 178°. After cooling, the solution is partitioned between diethyl ether and water, the ethereal layer washed again with water and saturated aqueous sodium chloride, and evaporated. The residue is taken up in 40 ml of methylene chloride and the solution treated with 2.6 g of pyridinium chlorochromate for 2 hours at 25°. The mixture is diluted with 100 ml of diethyl ether, filtered through a bed of infusorial earth and the filtrate evaporated, to yield the 2-[4-chloro-2-(2-fluorobenzoyl)-phenyl]-benzaldehyde.

Workup

  1. customThe starting material is prepared
  2. temperatureAfter cooling
  3. customthe solution is partitioned between diethyl ether and water
  4. washthe ethereal layer washed again with water and saturated aqueous sodium chloride
  5. customevaporated
  6. additionthe solution treated with 2.6 g of pyridinium chlorochromate for 2 hours at 25°
  7. additionThe mixture is diluted with 100 ml of diethyl ether
  8. filtrationfiltered through a bed of infusorial earth
  9. customthe filtrate evaporated

Sources & evidence

ORD record
ord-c48aed318dd94897afebdc710a4e0c8d
Source dataset
uspto-grants-1984_02
Patent number
US04434100

Reaction notes

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