1-Chloro-4-nitrobenzene → Methyl 5-chloro-2-nitrobenzeneacetate

HRID 1166002ノート

反応式

HRID 1166002 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.CN([S+](N(C)C)N(C)C)C.C[Si-](F)(F)(C)C.BrBr.S(=O)(O)[O-:30].[Na+].C1[CH2:38][O:37][CH2:36][CH2:35]1>C(#N)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH2:35][C:36]([O:37][CH3:38])=[O:30])([O-:10])=[O:9]

参加物

7

反応物 5

HCID 74741-Chloro-4-nitrobenzeneHCID 8028TetrahydrofuranHCID 24408BromineHCID 9795567Tris(dimethylamino)sulfonium difluorotrimethylsilicateHCID 23665763Sodium Bisulfite

生成物 1

HCID 13265167Methyl 5-chloro-2-nitrobenzeneacetate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 1.576 g (10 mmol) of 4-chloronitrobenzene and 1.68 mL (10.22 mmol) of carbomethyoxymethyltrimethylsilane in anhydrous THF was added 2.751 g (10 mmol) of TASF in 5 mL of acetonitrile at -78° C. The mixture was stirred for 7 hrs at that temperature, and 0.50 mL (9.70 mmol) of bromine was added dropwise. Stirring was continued for 1 hr, and saturated sodium bisulfite was added. The product was extracted into ether and isolated by chromatography on silica using 30% ether/hexane as solvent. The yield was 1.15 g (50%) product, which was an oil. The product was analyzed by infrared spectroscopy and nuclear magnetic resonance spectroscopy.

後処理

  1. additionwas added dropwise
  2. extractionThe product was extracted into ether
  3. customisolated by chromatography on silica using 30% ether/hexane as solvent

出典と根拠

ORDレコード
ord-1c839033c61345a096427acecd1e0003
出典データセット
uspto-grants-1990_03
特許番号
US04912220

反応ノート

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