Hydrochloric Acid → 7-Bromo-1-(5-chloro-2-hydroxyphenyl)-1-heptanone
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.ClC(Cl)C.Cl>C(Cl)Cl.ClCCCl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([C:26]1[CH:27]=[C:22]([Cl:21])[CH:23]=[CH:24][C:25]=1[OH:28])=[O:10].[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([C:26]1[CH:27]=[C:22]([Cl:21])[CH:23]=[CH:24][C:25]=1[O:28][CH3:29])=[O:9]Participants
Reactant 6
Product 2
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 45 °C
Procedure
A mixture of 7-bromoheptanoic acid (7.6 g, 36.4 mmol), oxalyl chloride (4 mL, 45.8 mmol) and 1,2-dichloroethane (80 mL) was stirred 45 minutes at approximately 25° C. and an additional 45 minutes at approximately 45° C. and then concentrated. The residue was stirred approximately 16 hours with a mixture of aluminum chloride (4.3 g, 32 mmol), 4-chloroanisole (4 g, 28 mmol) and dichloroethane (approximately 200 mL). The mixture was then poured over cold dilute hydrochloric acid and diluted with methylene chloride. The organic layer was separated, washed with water (3×) and dried (K2CO3). The residue was purified by column chromatography eluting with hexane/ethyl acetate (95:5) to give 7-bromo-1-(5-chloro-2-hydroxyphenyl)-1-heptanone (250 mg, 0.78 mmol), m.p. 79°-80° C. and 7-bromo-1-(5-chloro-2-methoxyphenyl)-1-heptanone (3.3 g, 9.9 mmol) as an oil.
Workup
- concentrationconcentrated
- customThe organic layer was separated
- washwashed with water (3×)
- dry with materialdried (K2CO3)
- customThe residue was purified by column chromatography
- washeluting with hexane/ethyl acetate (95:5)
Sources & evidence
- ORD record
- ord-4688456a8e944d8fb189dc480cb42699
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05739336
Reaction notes
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