Carbazole → HCID 20334397, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH:15]1[C:27]2NC3C(=CC=CC=3)C=2C=C[CH:16]=1.BrBr.BrC1C=CC2[N-]C3C(C=2C=1)=CC=CC=3.[Na+].BrCC#C>>[CH2:27]([N:6]1[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:15]#[CH:16]Participants
6
Procedure
Synthesis of 1,6-bis(N-3-bromocarbazolyl)-2,4-hexadiyne monomer was carried out by first preparing 3-bromocarbazole from carbazole and bromine. The product was converted to sodium 3-bromocarbazolide, which was then reacted with 3-bromo-1-propyne to give N-(2-propynyl)-3-bromocarbazole. Oxidative coupling of the propyne over cuprous chloride gave the desired monomer. Details of the reaction are given below.
Sources & evidence
- ORD record
- ord-d2db4734600e4cfc90eb52ff0a449e7f
- Source dataset
- uspto-grants-1980_06
- Patent number
- US04208501
Reaction notes
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