Ammonia → 2-(4-Chlorophenyl)-1-(4-fluoro-2-hydroxy-phenyl)-ethanone

HRID 14505

Reaction equation

HRID 14505 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[F:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.N>ClCCCl.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][C:19]=2[OH:23])=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 97433-FluorophenolHCID 906924-Chlorophenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 687025202-(4-Chlorophenyl)-1-(4-fluoro-2-hydroxy-phenyl)-ethanone

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-chlorophenylacetyl chloride (27.6 g, 0.15 mol) in 1,2-dichloroethane (200 ml), cooled to 0° C. in an ice bath, under nitrogen is added slowly AlCl3 (21.8 g, 0.16 mol). The reaction mixture is stirred at 0° C. for 20 min. 3-fluorophenol (12.2 g, 0.11 mol) is added, and the reaction mixture is allowed to warm to room temperature, then heated at 90° C. for 16 h. The reaction mixture is cooled to room temperature, then poured cautiously into aqueous ammonia solution (500 ml) with vigourous stirring. The mixture is diluted with CH2Cl2 (250 ml) and filtered through Celite. The organic phase is separated, washed with water, brine and dried (MgSO4). The solvent is removed in vacuo, and the crude product is purified by flash chromatography on silica gel using iso-hexane:ethyl acetate (10:1 to 4:1) as the eluent to give the title compound.

Workup

  1. temperatureto warm to room temperature
  2. temperatureheated at 90° C. for 16 h
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered through Celite
  5. customThe organic phase is separated
  6. washwashed with water, brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent is removed in vacuo
  9. customthe crude product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-44e1dcc8469d4abfa6010145fe0f0cf5
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Linked notes

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