Hydrochloric Acid → (3-Bromophenyl)(3-methylazulen-1-yl)methanone

HRID 1375964Notes

Reaction equation

HRID 1375964 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[C:15]2[C:9]([CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:8][CH:7]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21].Cl>C(Cl)Cl>[Br:16][C:17]1[CH:18]=[C:19]([C:20]([C:8]2[C:9]3[C:15]([CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]([CH3:5])[CH:7]=2)=[O:21])[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74377Benzoyl chloride, 3-bromo-HCID 1366111-MethylazuleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23080591(3-Bromophenyl)(3-methylazulen-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aluminum chloride (1.87 g) was added to a solution of 1-methylazulene (2 g) in methylene chloride (20 ml) at 0° C. and the mixture was stirred for 15 minutes. Then, a solution of 3-bromobenzoyl chloride (1.86 ml) in methylene chloride (5 ml) was added dropwise to the reaction mixture at 0° C. and the mixture was stirred for one hour. The reaction mixture was added to 10% aqueous solution of hydrochloric acid under cooling with ice and was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain (3-bromophenyl)(3-methylazulen-1-yl)methanone (1.2 g).

Workup

  1. stirringthe mixture was stirred for one hour
  2. temperatureunder cooling with ice
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9d01ea02f70642b4932f1211be59625e
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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