Acetic Acid → HCID 54245800, compound

HRID 1489927Notes

Reaction equation

HRID 1489927 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:7]=1[CH3:16])=[O:5].Br.[C:23](O)(=O)[CH3:24].[C:27](O)(=O)C>O>[CH:24]1([CH2:13][O:12][C:10]2[C:9]([O:14][CH3:15])=[CH:8][C:7]([CH3:16])=[C:6]([C:4](=[O:5])[C:3]3[C:2]([Cl:1])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:21])[CH:11]=2)[CH2:23][CH2:27]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11759162HCID 11759162, compound2×HCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 54245800HCID 54245800, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2,6-dichloro-4',5'-dimethoxy-2'-methylbenzophenone (Compound 1; 2.5 g, 7.7 mmol), hydrogen bromide/acetic acid (33%, 10 ml) and glacial acetic acid (10 ml) is stirred for 1.5 h at 75° C., poured into water (100 ml) and twice extracted with dichloromethane (50 ml each). The extracts are combined, dried, and concentrated in vacuo. The resulting oil is applied onto the top of a flash chromatography column (silica gel, 30 g). Elution is carried out with toluene and toluene/acetone, 9:1 (500 ml each). The fractions containing the material with an Rf =0.54 (silica gel; toluene/acetone, 9:1) are combined and the solvent is evaporated in vacuo until a final volume of 20 ml is reached. The solution is then extracted three times with aqueous sodium hydroxide (2N; 30 ml each). The aqueous layer is acidified with hydrochloric acid (6M) and the precipitate is collected by vacuum filtration and dried to give Compound 5 as colorless crystals, 1.1 g, (45.9% y) mp 152° C.

Workup

  1. extractiontwice extracted with dichloromethane (50 ml each)
  2. customdried
  3. concentrationconcentrated in vacuo
  4. washElution
  5. additionThe fractions containing the material with an Rf =0.54 (silica gel; toluene/acetone, 9:1)
  6. customthe solvent is evaporated in vacuo until a final volume of 20 ml
  7. extractionThe solution is then extracted three times with aqueous sodium hydroxide (2N; 30 ml each)
  8. filtrationthe precipitate is collected by vacuum filtration
  9. customdried

Sources & evidence

ORD record
ord-b3136464d62e48fe98fece1f714b7023
Source dataset
uspto-grants-1997_10
Patent number
US05679866

Reaction notes

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