Bromine → HCID 68577125, compound
Reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6])[CH3:2].[Br:11]Br>>[Br:11][C:8]1[CH:9]=[CH:10][C:3]([CH2:1][CH3:2])=[C:4]([CH:7]=1)[C:5]#[N:6]Participants
Procedure
9.74 ml of 2-ethylbenzonitrile are added dropwise to 100 g of Na-X zeolite (Linde 13X, STREM) with vigorous stirring. After the exothermic reaction, 5.6 ml of bromine are added dropwise at 55° C., add vigorous stirring of the mixture is continued. The temperature is kept at 45-50° C., by means of an ice bath. After the addition is complete, the ice bath is removed, and the mixture is stirred at 50° C. for 20 hours. 300 ml of methanol are added to the reaction mixture while stirring and the suspension is clarified by filtration through Hyflow. The filtrate is evaporated and the residue is partitioned between 100 ml of ethyl acetate and 50 ml of saturated sodium bicarbonate solution. The organic phase is dried with sodium sulphate, filtered and evaporated. The title compound is obtained as a beige crystalline solid from the residue by flash chromatography. Rt=4.87.
Workup
- additionare added dropwise at 55° C.
- additionadd vigorous
- customThe temperature is kept at 45-50° C., by means of an ice bath
- additionAfter the addition
- customthe ice bath is removed
- stirringthe mixture is stirred at 50° C. for 20 hours
- addition300 ml of methanol are added to the reaction mixture
- stirringwhile stirring
- filtrationthe suspension is clarified by filtration through Hyflow
- customThe filtrate is evaporated
- customthe residue is partitioned between 100 ml of ethyl acetate and 50 ml of saturated sodium bicarbonate solution
- dry with materialThe organic phase is dried with sodium sulphate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-28de2f52c5514087933b89a5567e0dfe
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07799779B2
Reaction notes
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