Hydrochloric Acid → 1-[3-(2-Chloroethoxy)-5-fluoro-2-nitrophenylmethanesulfonyl]-naphthalene

HRID 2219009노트

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HRID 2219009 반응식
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13].Cl[CH2:16][S:17]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)(=[O:19])=[O:18].CC(C)([O-])C.[K+].Cl>C1COCC1>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH2:16][S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:18])=[O:19])[CH:8]=[C:9]([F:11])[CH:10]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 23665647Potassium tert-butoxideHCID 431355982-(2-Chloroethoxy)-4-fluoro-1-nitrobenzene

생성물 1

HCID 598428001-[3-(2-Chloroethoxy)-5-fluoro-2-nitrophenylmethanesulfonyl]-naphthalene수율 88.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A mixture of 2-(2-chloroethoxy)-4-fluoro-1-nitro-benzene (1.3 g, 6 mmoles) and 1-chloromethane-sulfonyl-naphthalene (2.16 g, 9 mmoles) in THF, under nitrogen, was stirred at −78° C., treated dropwise with a solution of 1M potassium t-butoxide (18 ml, 18 mmoles) over a 30 min. period, allowed to warm to −40° C., stirred at −40° C. for 5 hours, poured into cold 2N HCl and extracted with EtOAc. The extracts were combined, dried over Na2SO4, and concentrated under vacuum. The resultant residue was recrystallized from CH2Cl2/hexane to afford the title compound as an off-white solid (2.25 g, 5.3 mmoles), identified by HNMR and mass spectral analyses.

후처리

  1. temperatureto warm to −40° C.
  2. stirringstirred at −40° C. for 5 hours
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe resultant residue was recrystallized from CH2Cl2/hexane

출처 및 근거

ORD 기록
ord-f6876681029143ee89f82713571ab346
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414051B2

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