Bromine → 4-Chloro-1,2-dicyanobenzene
Reaction equation
[Cl:1][CH:2]1[CH:9]=[CH:8][CH:5]([C:6]#[N:7])[CH:4]([C:10]#[N:11])[CH2:3]1.BrBr>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]#[N:11])[C:5](=[CH:8][CH:9]=1)[C:6]#[N:7]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 135 °C
Procedure
To a 1-l three-necked flask, equipped with a mechanical stirrer, a condenser with a gas outlet and an equa-pressured addition funnel, is charged 166.5 g (1 mole) of 4-chlorotetrahydrophthalonitrile and 75 g of chlorobenzene. The mixture is heated to 100°-110° C. with stirring. Bromine, 320 g (2 moles), is added dropwise into the mixture in a sub-surface manner. The red color of bromine dissipates quickly and a gas evolution starts. After about 240 g of bromine is added, the pot temperature is heated to 135° C. The addition of bromine continues until completion. The pot temperature is then raised to 165°-170° C. for 2-4 hours. During this period an additional amount of bromine, such as about 10 to 15 g, may be added to complete the conversion of 4-chlorotetrahydro-phthalonitrile. A good yield of 4-chlorophthalonitrile can be obtained by distilling out the chlorobenzene.
Workup
- customTo a 1-l three-necked flask, equipped with a mechanical stirrer, a condenser with a gas outlet and an equa-pressured addition funnel
- temperatureThe mixture is heated to 100°-110° C.
- temperatureThe pot temperature is then raised to 165°-170° C. for 2-4 hours
- additionsuch as about 10 to 15 g, may be added
Sources & evidence
- ORD record
- ord-9f3412858e484514bb0dd41b36860816
- Source dataset
- uspto-grants-1991_09
- Patent number
- US05049682
Reaction notes
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