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Tributylphosphine → {4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-3-chloro-phenyl}-acetic Acid Ethyl Ester

HRID 984943
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인쇄 미리보기

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HRID 984943 반응식
C(P(CCCC)CCCC)CCC.[CH2:14]([O:16][C:17](=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([Cl:26])[CH:20]=1)[CH3:15].[Br:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([C:39]2[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=2)=[CH:36][CH2:37]O)=[CH:31][CH:30]=1>C1COCC1>[CH2:14]([O:16][C:17](=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:37][CH:36]=[C:35]([C:32]2[CH:31]=[CH:30][C:29]([Br:28])=[CH:34][CH:33]=2)[C:39]2[CH:40]=[CH:41][C:42]([Br:45])=[CH:43][CH:44]=2)=[C:21]([Cl:26])[CH:20]=1)[CH3:15]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 13831TributylphosphineHCID 11031224Ethyl 3-chloro-4-hydroxyphenylacetateHCID 222703043,3-Bis-(4-bromophenyl)prop-2-en-1-ol

생성물 1

HCID 10120503{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-3-chloro-phenyl}-acetic Acid Ethyl Ester수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
2.5 °C

실험 절차

A solution of tributylphosphine (955 μl, 3.0 mmol), 3-chloro-4-hydroxyphenylacetic acid ethyl ester (472 mg, 2.2 mmol) and 3,3-bis-(4-bromophenyl)prop-2-en-1-ol (736 mg, 2.0 mmol) in dry THF (15 ml) was stirred at 0-5° C. for 30 min, under a atmosphere of nitrogen. Azodicarboxylic dipiperidide (756 mg, 3.0 mmol) was added the mixture stirred at 0-5° C. for 2 h, and at room temperature over night. The reaction mixture was filtered and the filtrate concentrated in vacuo. The crude product was then purified by column chromatography on silica (eluent graduated from heptane to toluene) to give 1.0 g (89%) of the title compound.

후처리

  1. waitat room temperature over night
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe crude product was then purified by column chromatography on silica (eluent graduated from heptane to toluene)

출처 및 근거

ORD 기록
ord-747732c38f2f4f44ace3fc8d8176d064
출처 데이터셋
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06869967B2

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