1-Methylimidazole → 1-(3-Chloro-4-fluorophenyl)propan-2-one

HRID 514101

Reaction equation

HRID 514101 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:13]N1C=CN=C1>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](=[O:12])[CH3:13])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 27737212-(3-Chloro-4-fluorophenyl)acetic acid

Product 1

HCID 552735661-(3-Chloro-4-fluorophenyl)propan-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 2-(3-chloro-4-fluorophenyl)acetic acid (18.46 g, 97.89 mmol) in acetic anhydride (463 mL) was added N-methylimidazole (3.9 mL) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution and organic layer was concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a colorless oil (14.5 g, 79%). 1H NMR (400 MHz, CDCl3) δ 7.23 (dd, J=6.9, 2.1 Hz, 1H), 7.14-7.00 (m, 2H), 3.66 (s, 2H), 2.19 (s, 3H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate solution and organic layer
  2. concentrationwas concentrated
  3. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6c2c69c9e4604669bf78354308ba7cf5
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Linked notes

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