5-Bromo-2-chlorobenzoyl chloride → HCID 86685116, compound

HRID 1912999Notes

Reaction equation

HRID 1912999 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH2:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[F:22])[CH3:13].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([C:7]([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:12][CH3:13])=[C:16]([F:22])[C:17]=2[F:21])=[O:8])[CH:10]=1

Participants

5

Reactant 3

HCID 27568715-Bromo-2-chlorobenzoyl chlorideHCID 27829281-Ethoxy-2,3-DifluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86685116HCID 86685116, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-bromo-2-chloro-benzoyl chloride 2a (7.74 g, 30.5 mmol) was dissolved in 200 mL dichloromethane, followed by addition of 1-ethoxy-2,3-difluoro-benzene 3b (4.82 g, 30.5 mmol) and aluminum trichloride (4.07 g, 30.5 mmol). The reaction mixture was stirred for 16 hours. Thereafter, the mixture was partitioned after 100 mL 2 M hydrochloric acid were added. The organic extract was washed with saturated sodium chloride solution (100 mL) and combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (5-bromo-2-chloro-phenyl)-(4-ethoxy-2,3-difluoro-phenyl)methanone 3c (8.0 g, yellow grease), yield: 70.2%. MS m/z (ESI): 376.9 [M+1].

Workup

  1. customThereafter, the mixture was partitioned after 100 mL 2 M hydrochloric acid
  2. additionwere added
  3. extractionThe organic extract
  4. washwas washed with saturated sodium chloride solution (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-91fb6dc8c31d4c708b5a75116b507c21
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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