Acetyl chloride → 3,6-Diacetyl-9-ethylcarbazole

HRID 542704

Reaction equation

HRID 542704 reaction equation
C(C1C=CC2N(CC)C3C(C=2C=1)=CC(C=C)=CC=3)=C.[CH2:20]([N:22]1[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH3:21].[Cl-].[Al+3].[Cl-].[Cl-].[C:39](Cl)(=[O:41])[CH3:40].[C:43](Br)(=[O:45])[CH3:44].[BH4-].[Na+].P(Cl)(Cl)(Cl)=O>C(=S)=S.CN(C)C1C=CN=CC=1.N1C=CC=CC=1.CC(O)C>[C:39]([C:26]1[CH:25]=[CH:24][C:23]2[N:22]([CH2:20][CH3:21])[C:34]3[C:29]([C:28]=2[CH:27]=1)=[CH:30][C:31]([C:43](=[O:45])[CH3:44])=[CH:32][CH:33]=3)(=[O:41])[CH3:40]

Participants

12

Reactant 7

HCID 6367Acetyl chlorideHCID 6836N-ethyl carbazoleHCID 10482Acetyl bromideHCID 24813Phosphorus oxychlorideHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) ChlorideHCID 139071523,6-Diethenyl-9-ethyl-9H-carbazole

Product 1

HCID 6220833,6-Diacetyl-9-ethylcarbazole

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 3776IsopropanolSolventHCID 6348Carbon DisulfideSolvent

Procedure

Another preferred example, also for use in a photoresist application, is a 3,6-divinyl-N-ethylcarbazole. 3,6-Diacetyl-N-ethylcarbazole is prepared by treating a mixture of N-ethylcarbazole and aluminum chloride in carbon disulfide with a mixture of acetyl chloride and acetyl bromide. The crude product is converted with sodium borohydride in refluxing 2-propanol to the corresponding secondary diol, which is in turn refluxed with phosphorus oxychloride and 4-dimethylaminopyridine in pyridine to afford the monomer as long white needles, MP 88°-93° C., after purification.

Workup

  1. additionby treating

Sources & evidence

ORD record
ord-d958db557c614388a74edbe596575656
Source dataset
uspto-grants-1987_04
Patent number
US04659648

Linked notes

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