Diethyl Ether → HCID 18470194, compound
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14].[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)C>ClCCl>[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=1)=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a stirring suspension of aluminium chloride (33.6 g) in dry dichloromethane (474 ml) was added 8-bromo-n-octanoyl chloride (67.8 g) over 10 min. Chlorobenzene (123 ml) was then added over 10 min and the mixture allowed to stir at 25° C. for 74 h and stood for 64 h. The mixture was poured into ice/water (540 ml) and diethyl ether (1.3 L). The organic layer was removed and was washed with water (540 ml), saturated sodium hydrogen carbonate (540 ml), water (400 ml) and brine (400 ml) and dried over magnesium sulfate. Removal of the organic layer under reduced pressure and chromatography of the residue on silica gel using 5% ethyl acetate in hexane gave 8-bromo-1-(4-chlorophenyl)octan-1-one (35.5 g). 1H-NMR (CDCl3) δ 1.2-1.6 (6H, m), 1.6-1.95 (4H, m), 2.95 (2H, t), 3,42 (2H, t), 7.43 (2H, m) and 7.90 (2H, m).
Workup
- waitstood for 64 h
- customThe organic layer was removed
- washwas washed with water (540 ml), saturated sodium hydrogen carbonate (540 ml), water (400 ml) and brine (400 ml)
- dry with materialdried over magnesium sulfate
- customRemoval of the organic layer under reduced pressure and chromatography of the residue on silica gel using 5% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-1eacd88017284f9b87750181242571e7
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06417192B1
Reaction notes
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