Chlorobenzene → HCID 18376484, compound

HRID 2300664Notes

Reaction equation

HRID 2300664 reaction equation
[Cl-].[CH3:2][O:3][C:4](=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O.[Al](Cl)(Cl)Cl.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:9]([CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH3:2])=[O:12])=[O:11])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 24012Aluminum ChlorideHCID 86645753HCID 86645753, compound

Product 1

HCID 18376484HCID 18376484, compound

Procedure

Adipic acid monomethyl ester chloride (17.9 g) was added dropwise into a mixture of chlorobenzene(33.8 g) and aluminum chloride anhydrous(26.7 g) with cooling with ice. After stirring for 2 hours, the reaction mixture was poured into ice water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried (MgSO4). The solvent was evaporated to give methyl 5-(4-chlorobenzoyl)pentanoate. This was dissolved into dichloromethane(100 ml), thereto bromine(16.0 g) was added dropwise. The reaction mixture was washed with water and then with sodium hydrogensulfite. The dichloromethane layer was washed with water, and dried (MgSO4). The solvent was evaporated to give methyl 5-bromo-5-(4-chlorobenzoyl)pentanoate(31.7 g, 95%) as an oily substance.

Workup

  1. temperaturewith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-234687357f2045ca91ebf878c9021231
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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