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Diethyl Ether → Methoxycarbonylaminooxyacetic acid 2,6-dibromo-4-cyano-phenoxycarbonyloxymethyl ester

HRID 843099
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HRID 843099 반응식
[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([Br:10])[C:3]=1[O:11][C:12](=[O:16])[O:13][CH2:14]I.[CH3:17][O:18][C:19]([NH:21][O:22][CH2:23][C:24]([O-:26])=[O:25])=[O:20].[Na+].CCOCC>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([Br:10])[C:3]=1[O:11][C:12]([O:13][CH2:14][O:26][C:24](=[O:25])[CH2:23][O:22][NH:21][C:19]([O:18][CH3:17])=[O:20])=[O:16]
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참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 23677256Sodium methoxycarbonylaminooxyacetateHCID 70170991Carbonic acid iodomethyl ester 2,6-dibromo-4-cyanophenyl ester

생성물 1

HCID 86757969Methoxycarbonylaminooxyacetic acid 2,6-dibromo-4-cyano-phenoxycarbonyloxymethyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of carbonic acid iodomethyl ester 2,6-dibromo-4-cyanophenyl ester (0.20 g, 0.43 mmol) in DMF (2 mL) was added sodium methoxycarbonylaminooxyacetate (0.89 g, 0.52 mmol). The mixture was stirred for 16 h. Ether was added to the reaction and washed with water then brine then dried over sodium sulfate, filtered, and concentrated to an oil. Silica gel chromatography (2:1 EtOAc:hexanes) afforded the desired product as a clear oil. 1H-NMR (300 MHz, CDCl3) δ (ppm): 3.80 (s, 3H), 4.57 (s, 2H), 5.99 (s, 2H), 7.90 (s, 2H), 8.02 (bs, 1H). Mp=110-111° C.

후처리

  1. washwashed with water
  2. dry with materialbrine then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to an oil

출처 및 근거

ORD 기록
ord-2b22ff78a94145128fccdca38492e89b
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06376548B1

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