Carbazole → HCID 66717043, compound

HRID 1776065Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30].C1C2NC3C(=CC=CC=3)C=2C=CC=1>>[OH:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

Reactant 3

HCID 6854Carbazole

HCID 1626071-Octanol, 8-bromo-

HCID 667170719-Phenyl-9H-carbazol-3-ol

Product 1

HCID 66717043HCID 66717043, compoundYield 84.3%

Procedure

Demethylate 3-methoxy-9-phenylcarbazole (E-4) in the same manner as in Synthesis of Carbazole Derivative 1 to obtain 3-hydroxy-9-phenylcarbazole (E-5) having a colorless needle-like form with a yield of 91.8%; etherify the thus obtained 3-hydroxy-9-phenylcarbazole having a colorless needle-like form with 8-bromooctanol in the same manner as in Synthesis of Carbazole Derivative 2 to obtain 3-(8-hydroxyoctyloxy)-9-phenyl carbazole (E-6) having a colorless needle-like form with a yield of 84.3%; tosylate, thioacetylate, and hydlolyze the thus obtained 3-(8-hydroxyoctyloxy)-9-phenyl carbazole in the same manner as in Synthesis of Carbazole Derivative 2 to obtain 3-(8-meracaptooctyloxy)-9-phenyl carbazole (E-9) (hereinafter referred to as carbazole derivative 3) having a colorless needle-like form represented by the chemical structure 9.

Sources & evidence

ORD record: ord-b4b788903414412fbc6991f8997026fa
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09263682B2

Reaction notes

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