4-Aminophenol → 4-Aminophenoxy-4'-phenylethynylbenzophenone

HRID 35986

반응식

HRID 35986 반응식
[C:1]1([C:7]#[C:8][C:9]2[CH:23]=[CH:22][C:12]([C:13]([C:15]3[CH:20]=[CH:19][C:18](F)=[CH:17][CH:16]=3)=[O:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:13]([C:12]2[CH:22]=[CH:23][C:9]([C:8]#[C:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:10][CH:11]=2)=[O:14])=[CH:27][CH:26]=1

참가 물질

5

반응물 3

HCID 4034-AminophenolHCID 11430Potassium CarbonateHCID 40956574-Fluoro-4'-(phenylethynyl)benzophenone

생성물 1

HCID 544968244-Aminophenoxy-4'-phenylethynylbenzophenone

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

The phenylethynyl group has two important advantages over the ethynyl group. These are stability towards conditions of aromatic nucleophilic displacement reactions and stability at moderate temperatures (i.e. 150-250° C.). For example, when 4-phenylethynyl-4'-fluorobenzophenone was treated with a slight excess of 3 or 4-aminophenol in the presence of an alkali metal base such as potassium carbonate in a polar aprotic solvent such as N,N-dimethylacetamide (DMAc) at 143° C., 3 or 4-aminophenoxy-4'-phenylethynylbenzophenone was afforded in nearly quantitative yield. However, several attempts to make the 3-aminophenoxy-4'-ethynylbenzophenone from the 4-ethynyl-4'-fluorobenzophenone under similar reaction conditions afforded a mixture of products. In addition, imide model compounds of the phenylethynyl endcapper react at a moderate to fast rate in air at 300° to 350° C. whereas analogous model compounds containing the ethynyl group react at a moderate to fast rate in air at 200° to 250° C. Phenylethynyl containing imide model compounds are reasonably stable at 200° C. (see Example 6) whereas thynyl containing imide model compounds react at 200° C.

후처리

  1. customat moderate temperatures (i.e. 150-250° C.)
  2. customat 143° C.

출처 및 근거

ORD 기록
ord-5264557d0e934eab82b17a6d29d127c5
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412066

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