Hydrochloric Acid → 2-(4-Bromophenyl)-1-(2,4-dichlorophenyl)ethanone

HRID 1982934Notes

Reaction equation

HRID 1982934 reaction equation
[Na].C[Si](C)(C)N[Si](C)(C)C.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1.COC(=O)[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32].Cl>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])=[O:21])=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 37055Methyl 2,4-dichlorobenzoateHCID 74654Benzeneacetic acid, 4-bromo-HCID 5360545Sodium

Product 1

HCID 634923632-(4-Bromophenyl)-1-(2,4-dichlorophenyl)ethanoneYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

436 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF is cooled to −60° C., in a nitrogen atmosphere, 400 ml of THF is added then, dropwise, a solution of 75 g of 4-bromophenylacetic acid in 100 ml of THF and it is stirred for 1 h 30 min at −70° C. Then 67.9 g of methyl-2,4-dichlorobenzoate is added dropwise, stirred for 30 minutes, then the temperature is allowed to rise to 5° C. The reaction mixture is poured onto a mixture of ice/1 liter of 2N HCl, extracted with ether, the organic phase is washed with a saturated NaHCO3 solution, then with water, dried over Na2SO4 and the solvent is evaporated under vacuum to a volume of 200 ml, pentane is added and the crystalline product that forms is dried. 80 g of the expected compound is obtained.

Workup

  1. additionis added
  2. customto rise to 5° C
  3. extractionextracted with ether
  4. washthe organic phase is washed with a saturated NaHCO3 solution
  5. dry with materialwith water, dried over Na2SO4
  6. customthe solvent is evaporated under vacuum to a volume of 200 ml, pentane
  7. additionis added
  8. customthe crystalline product that forms is dried

Sources & evidence

ORD record
ord-b2f16bf32a054acda8fc34d51a6f6c44
Source dataset
uspto-grants-2009_06
Patent number
US07541361B2

Reaction notes

Loading…