5-Bromo-2-chlorobenzoyl chloride → (5-Bromo-2-chloro-phenyl)-[5-(4-fluorophenyl)-2-thienyl]methanone

HRID 1913059Notes

Reaction equation

HRID 1913059 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:7]=[CH:8][C:9]([Cl:15])=[C:10]([CH:14]=1)[C:11](Cl)=[O:12].[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[CH:19][CH:18]=1>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([Cl:15])=[C:10]([C:11]([C:25]2[S:24][C:23]([C:20]3[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=3)=[CH:27][CH:26]=2)=[O:12])[CH:14]=1

Participants

5

Reactant 3

HCID 27568715-Bromo-2-chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 218947832-(4-Fluorophenyl)thiophene

Product 1

HCID 86685156(5-Bromo-2-chloro-phenyl)-[5-(4-fluorophenyl)-2-thienyl]methanoneYield 37.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

AlCl3 (1.5 g, 11 mmol) was dissolved in 10 mL methylene chloride and cooled to −10° C., followed by addition of 5-bromo-2-chloro-benzoyl chloride 2a (2.54 g, 10 mmol) and 2-(4-fluorophenyl)thiophene 9b (1.78 g, 10 mmol). The reaction mixture was stirred for 30 minutes and then warmed to room temperature and stirred for another 16 hours. Thereafter, the reaction mixture was cooled to −10° C. The reaction mixture was extracted with ethyl acetate (50 mL×2) after a small amount of water and 20 mL 1 M hydrochloric acid were added. The organic extracts were combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system B to obtain the title compound (5-bromo-2-chloro-phenyl)-[5-(4-fluorophenyl)-2-thienyl]methanone 9c (1.5 g, yellow solid), yield: 37.9%.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for another 16 hours
  3. temperatureThereafter, the reaction mixture was cooled to −10° C
  4. extractionThe reaction mixture was extracted with ethyl acetate (50 mL×2) after a small amount of water and 20 mL 1 M hydrochloric acid
  5. additionwere added
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe resulting residue was purified by silica gel chromatography with elution system B

Sources & evidence

ORD record
ord-240eb617cbd547599c069413a85720b1
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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