Carbazole → 3-Bromocarbazole

HRID 542703Notes

Reaction equation

HRID 542703 reaction equation
C([C:4]1[CH:5]=[CH:6][C:7]2[N:8](C[Si](C)(C)C)[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)C=C.C1C2NC3C(=CC=CC=3)C=2C=CC=1.[Br:35]Br.[H-].[Na+].ClC[Si](C)(C)C.C([Li])CCC>N1C=CC=CC=1.O1CCCC1.CC(C)=O>[Br:35][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

10

Reactant 6

HCID 6854CarbazoleHCID 24408BromineHCID 24758Sodium hydrideHCID 75361Silane, (chloromethyl)trimethyl-HCID 13907156HCID 13907156, compoundHCID 178418339Butyllithium

Product 1

HCID 2524463-Bromocarbazole

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1049PyridineSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A preferred example is the use of 3-(2-propenyl)-N-trimethylsilylmethylcarbazole as the polymerizable monomer in a photoresist. 3-Bromocarbazole is prepared by treating carbazole in pyridine with a solution of bromine in pyridine. The purified product is converted to the N-trimethylsilylmethyl derivative by sequential treatment in tetrahydrofuran with sodium hydride and chloromethyltrimethylsilane, followed by refluxing. The purified product is treated with n-butyllithium, acetone, and worked up to give an intermediate alcohol, which is converted to 3(2-propenyl)-N-trimethylsilylmethylcarbazole by treatment with thionyl chloride in pyridine at 50° C. The product is purified by column chromatography to give a very viscous liquid.

Workup

  1. temperatureby refluxing

Sources & evidence

ORD record
ord-b65ca2ebc3f147dd99bc6e4dd776f4ff
Source dataset
uspto-grants-1987_04
Patent number
US04659648

Reaction notes

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