Hydrochloric Acid → 3,5-Diethyl-1-bromobenzene
Reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH2:9][CH3:10])[C:5](N)=[C:4]([CH2:11][CH3:12])[CH:3]=1.Cl.N([O-])=O.[Na+].O[PH2]=O>O.CCO.C(O)(=O)C>[CH2:11]([C:4]1[CH:3]=[C:2]([Br:1])[CH:8]=[C:7]([CH2:9][CH3:10])[CH:5]=1)[CH3:12]Participants
8
Conditions
- Temperature
- -5 °C
Procedure
A mixture of 20 g of 4-bromo-2,6-diethylaniline, 160 ml of acetic acid, 100 ml of concentrated HCl solution, 30 ml of water and 100 ml of EtOH is cooled to −5° C., a solution of 6.6 g of sodium nitrite in 25 ml of water is added dropwise and the mixture is left stirring at RT for 30 minutes. The reaction mixture is poured into 170 ml of 50% H3PO2 cooled to 0° C. and is left stirring for 2 hours at 0° C. and then for 48 hours at RT. The reaction mixture is extracted with ether, the organic phase is washed with water, with 1N NaOH solution, with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with cyclohexane. 18 g of the expected product are obtained.
Workup
- waitthe mixture is left
- temperaturecooled to 0° C.
- waitis left
- stirringstirring for 2 hours at 0° C.
- waitfor 48 hours at RT
- extractionThe reaction mixture is extracted with ether
- washthe organic phase is washed with water, with 1N NaOH solution, with water
- dry with materialdried over Na2SO4
- customthe solvent is evaporated off under vacuum
- customThe residue is chromatographed on silica gel
- washeluting with cyclohexane
Sources & evidence
- ORD record
- ord-9027dcd0ed55406e92ef7b8714859fbb
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642233B1
Reaction notes
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