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Product Details
The invention belongs to the field of organic synthesis, and relates to synthesis of a photoelectric material intermediate N-(7-bromine-9, 9-dimethyl fluorene-2-yl) carbazole. The method comprises thefollowing steps of coupling 4-carbazolylphenylboronic acid and 5-bromine-2-iodobenzoic acid methyl ester, generating a methylation product by using a Grignard reagent, and finally performing Friedel-Crafts reaction and cyclization by using aluminum trichloride to obtain a target product. According to the method, the reaction temperature is reduced, the selectivity of bromine and iodine is improved, the purity and yield are improved, and the yield reaches 87% or above. The cost is reduced, and the method is suitable for industrial production.
4-(carbazol-9-yl)phenylboronic acid
9,9-dimethyl-7-(9H-9-carbazolyl)-2-bromofluorene
| Conditions | Yield |
|---|---|
|
Multi-step reaction with 3 steps
1: potassium fluoride dihydrate; tetrakis(triphenylphosphine) palladium(0) / dimethyl sulfoxide; tetrahydrofuran; water / 8 h / Inert atmosphere; Reflux
2: tetrahydrofuran / 4 h / 20 - 25 °C / Inert atmosphere
3: aluminum (III) chloride / dichloromethane / 0.5 h / 0 - 5 °C
With
aluminum (III) chloride; tetrakis(triphenylphosphine) palladium(0); potassium fluoride dihydrate;
In
tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;
|
9,9-dimethyl-7-(9H-9-carbazolyl)-2-bromofluorene
3-chlorophenylboronic acid
C33H24ClN
| Conditions | Yield |
|---|---|
|
With
tetrakis(triphenylphosphine) palladium(0); potassium carbonate;
In
tetrahydrofuran; water;
at 80 ℃;
for 8h;
Inert atmosphere;
|
98% |
4-(carbazol-9-yl)phenylboronic acid
C51H38N2
C33H26N2
C51H36N2S
2-(3',5'-dibromophenyl)-7-(9H-9-carbazolyl)-9,9-dimethyl-fluorene
CAS:25550-51-0
Molecular Formula:C<sub>9</sub>H<sub>12</sub>O<sub>3</sub>
Molecular Weight:168.19
CAS:955959-91-8
CAS:333432-28-3
Molecular Formula:C15H15BO2
Molecular Weight:238.09
