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

HRID 1055581Notes

Reaction equation

HRID 1055581 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-].[Al+3].[Cl-].[Cl-]>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 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-chlorobenzoyl chloride 21d (3.41 g, 13.4 mmol) and 1-ethoxy-2,3-difluoro-benzene 23b (2.42 g, 15.2 mmol) in dichloromethane (50 mL) was added anhydrous aluminium chloride (1.82 g, 13.7 mmol) in portions over 1 hours at 0° C. The mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched with hydrochloric acid (10 mL, 2 M) and extracted with dichloromethane (40 mL×4). The combined layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 23d as yellow oil (5.03 g, 100%). This material was not further purified.

Workup

  1. customThe reaction mixture was quenched with hydrochloric acid (10 mL, 2 M)
  2. extractionextracted with dichloromethane (40 mL×4)
  3. dry with materialThe combined layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f3287cde4d414959af9a0dc0469ac088
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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