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Triethylamine → 3-Hydroxy-1-[4-chloro-2-(2-fluorobenzoyl)phenyl]propyne methanesulfonate

HRID 2417568
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HRID 2417568 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([OH:4])(=[O:6])=[O:3].[OH:6][CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 128416493-Hydroxy-1-[4-chloro-2-(2-fluorobenzoyl)phenyl]propyne

생성물 1

HCID 867382813-Hydroxy-1-[4-chloro-2-(2-fluorobenzoyl)phenyl]propyne methanesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Dropwise 13 ml (0.17 mole) of methanesulfonyl chloride was added to a solution of 28.9 g (0.1 mole) of 3-hydroxy-1-[4-chloro-2-(2-fluorobenzoyl)phenyl]propyne and 24.4 ml (0.175 mole) of triethylamine in 300 ml of methylene chloride which was cooled to 0° C. The mixture was washed with ice water, cold 1N hydrochloric acid, cold saturated aqueous sodium bicarbonate and dried over anhydrous sodium sulfate. Concentration of the methylene chloride solution gave a brown oil which was crystallized from ether to give a yellow solid. Recrystallization from a mixture of ether and petroleum ether gave off-white prisms, mp 95°-96° C.

후처리

  1. washThe mixture was washed with ice water, cold 1N hydrochloric acid, cold saturated aqueous sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. customConcentration of the methylene chloride solution gave a brown oil which
  4. customwas crystallized from ether
  5. customto give a yellow solid
  6. customRecrystallization
  7. additionfrom a mixture of ether and petroleum ether
  8. customgave off-white prisms, mp 95°-96° C.

출처 및 근거

ORD 기록
ord-2d046880ae2f4596a2bed50c53e8b9d5
출처 데이터셋
uspto-grants-1984_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04469633

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