Hydrochloric Acid → 3',5'-Dichloroacetophenone

HRID 1865411Notes

Reaction equation

HRID 1865411 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[C:5](N(OC)C)=[O:6].[CH3:15][Mg]Br.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH3:15])[CH:11]=[C:12]([Cl:14])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 587973333,5-Dichloro-N-methoxy-N-methylbenzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 27580583',5'-Dichloroacetophenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the product from step A (5.42 g, 23.2 mmol) in 100 mL of tetrahydrofuran was added methylmagnesium bromide (11.6 mL, 34.8 mmol) drop-wise. After stirring at ambient temperature for 25 min, 1N hydrochloric acid was added and the mixture extracted with two portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to provide the title compound which was used without further purification. 1H NMR (500 MHz, CDCl3) δ: 7.84 (d, J=1.9 Hz, 2H); 7.58 (d, J=1.8 Hz, 1H); 2.63 (s, 3H).

Workup

  1. extractionthe mixture extracted with two portions of ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b57a569bbe5b4bebbd9de99fd9714405
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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