Hydrochloric Acid → 2-Chloro-1-(2,4-difluoro-5-methylphenyl)ethan-1-one

HRID 1784936

Reaction equation

HRID 1784936 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:14][CH2:15][C:16](Cl)=[O:17].Cl>CCOC(C)=O.O>[Cl:14][CH2:15][C:16]([C:5]1[CH:4]=[C:3]([CH3:9])[C:2]([F:1])=[CH:7][C:6]=1[F:8])=[O:17]

Participants

7

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 2,4-difluorotoluene was added 6.3 g (47.3 mmol) of AlCl3, and 3.4 mL (42.6 mmol) of chloroacetyl chloride at 0° C. After the mixture was stirred for 10 min. at 0° C. and then at 45° C. for 30 min. The mixture was allowed to cool to r.t., about 16 mL of conc. HCl, 25 mL of water, and 100 mL of EtOAc were added. The organic layer was separated and washed with brine and sat. NaHCO3 (2×), and dried over Na2SO4. The solution was filtered and concentrated to give 9.0 g of 2-chloro-1-(2,4-difluoro-5-methylphenyl)ethanone as a colorless solid that was used without further purification.

Workup

  1. waitat 45° C. for 30 min
  2. temperatureto cool to r.t.
  3. customThe organic layer was separated
  4. washwashed with brine and sat. NaHCO3 (2×)
  5. dry with materialdried over Na2SO4
  6. filtrationThe solution was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8235be2de36244b5931c0eec595e522e
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Linked notes

Loading…